Longboat Key Condos For Rent - 72 condos

Remarks: A little slice of Gulf-front heaven. Seasonal rental only, available July 15 through December 31, 2026! 60 Day Minimum Lease, not available Jan 1, 2027-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches are perfectly complemented by the beautifully redesigned interior and thoughtfully updated floor plan. The gathering room opens to the extended kitchen to create continuity in the main living area, perfect for entertaining. Custom imported cabinetry with frosted glass accents, pantry storage, complementary upper and lower cabinetry, solid surface countertops, and a waterfall-edge peninsula with seating for four elevate the space. Premium KitchenAid appliances include a French door refrigerator, dishwasher, double oven, and cooktop. A skylight fills the home with natural light alongside LED, recessed, and drop lighting throughout. Imported marble flooring, porcelain tile, and neutral Berber carpet complete the interior finishes. Both bathrooms have been beautifully modernized with Corinthian Fossil showers, frameless glass doors, floating vanities, and Quartz countertops. The primary en suite features a walk-in closet and sitting area. Multiple sets of sliding glass doors open to the covered balcony, creating the perfect place to enjoy our million dollar sunsets. Residents can unwind seaside along more than 500 feet of shoreline, stroll the lushly landscaped grounds and paver pathways, or enjoy the private community pool and spa. All lease terms shorter than 6 months are subject to 13% tourism tax.

Listing is courtesy of: TNG PROPERTY MANAGEMENT (941-773-9599)

Listing Agent: Scott Nold (941-773-9599)

Remarks: Booked Dec 1st 2026-March 31st 2027. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private beach. Under-building assigned parking directly across from security coded entry lobby with elevator and mailboxes. Plenty of guest parking inside the welcome security gates. Full time maintenance crew keeps the grounds immaculate. Wake up to beach and water views from Living room, both bedrooms and terrace. The apartment has an fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room furniture, decor and linens. Utility room with Maytag washer and dryer. Sunset Beach is currently replacing all lobby and hallway flooring. Just minutes to St Armand’s Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel.

Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)

Listing Agent: Jennifer Le Blanc (941-400-0374)

Remarks: Available 05/01/2026 through 12/30/2026 FOR $5000. LEASED SEASON JAN, 2026 THROUGH MARCH, 2027. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais, walk in closets. Double queen beds in one of the ensuites. open floor plan features large eat in area with granite counters neutral tile floors, and extra storage outside unit. Laundry is located right outside of your unit. Covered Carport and guest parking available. Building amenities WIFI, renovated social room and fitness center. Resort style living with heated Olympic size pool, tennis courts, biking trails, and outside showers. Enjoy the Publix Grocery just minutes away along with many restaurants for fine dining. This building is located the furthest South end of Longboat Key so you miss a lot of traffic. Just minutes to St. Armand's Circle for shopping, restaurants and entertaining. Enjoy Lido Beach also just minutes away.

Listing is courtesy of: CHROME REALTY LLC (941-363-6300)

Listing Agent: Marni Hayden (941-809-5044)

Remarks: Must read entirely. 2026 RENTAL- Not Available until Nov 2026. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so you can bring your boat! The home was newly renovated with space and comfort in mind. The Master has a king size bed and a great view of the canal! The screened in porch overlooks the intercoastal with all its wildlife. Try out Sarasota and stay on the beach! St. Armand’s circle is nearby with world class shopping/dining and entertainment. Cleaning fee/resort taxes not included. HOA application with background and credit check required. NO PETS. NON SMOKING UNIT. Not available for less than 2 months. Available for 3 months or longer at a discount for $5,000/monthly. Vacation rental rates: December -April: $6,000; and May: $4,500. 2-month minimum stay during peak season (December through April).

Listing is courtesy of: AG REALTY SERVICES LLC (407-374-7295)

Listing Agent: Armando Gonzalez (407-346-6229)

Remarks: SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST ARMANDS CIRCLE of restaurants, shops and entertainment.

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: Jane Hunter (941-896-0622)

Remarks: SEASONAL: 90 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is beautifully renovated with professionally designed interior. Sip your morning coffee on the balcony with new glass railings as you plan your daily adventures. The light and bright living room features exquisite leather recliners and fabric sofas, one of which is a sleeper for an extra guest. Thoughtfully planned, you'll enjoy state of the art digital components including 85-inch TV and DVR while relaxing.Entertaining is a delight in the gourmet kitchen with stainless appliances. Escape to the tranquil master bedroom retreat with exquisite bedding overlooking azure waters with 65 inch smart TV, sitting area and ensuite master bath. For added comfort during your stay there’s a dedicated desk, stacked washer and dryer, built-in closet systems, wifi and 65' large smart tv in guest suite. Parking is conveniently located at the building's front door. Live the life you’ve always imagined with resort-style amenities that include Gulf-side heated pool, har-tru tennis court, updated social room, state of the art fitness area and kayak, paddle board & bike storage. Conveniently located to shopping, dining, St. Armand’s Circle and downtown Sarasota and the Arts. No pets or smoking permitted. Owners update every year...new flooring, dish washer and A/C system! BOOKED JAN - MAR 2027.

Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)

Listing Agent: Diann Thelen (941-920-0758)

Remarks: LONGBOAT KEY CLUB – GULF FRONT LUXURY RENTAL Enter the private, gated community of Longboat Key Club and experience true coastal paradise with breathtaking Gulf-front views. This completely remodeled 2-bedroom, 2-bath condominium showcases elegant, high-end finishes throughout. The bright and open living area features stunning marble flooring and walls, with expansive windows and a large private balcony that perfectly frame the panoramic ocean views. The modern kitchen has been thoughtfully redesigned with a sleek style, offering a large island and seamless flow into the living and dining areas—ideal for entertaining. The dining room also enjoys beautiful water views, creating the perfect backdrop for every meal. The spacious primary suite is a private retreat, while the luxurious primary bathroom makes a bold statement with striking marble finishes. The second bedroom is generously sized and comfortably accommodates double beds. Residents enjoy resort-style amenities including a heated beachfront pool and spa, a state-of-the-art fitness center, sauna, steam room, and 24-hour security. Available for 3- to 6-month stays.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-360-7777)

Listing Agent: Lily Behrends (941-526-9121)

Remarks: SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite features King-sized bed, TV, & opens to a private balcony. The comfortable guest bedroom offers a Queen and 1 twin bed with ceiling fan, and guest bathroom with tub/shower. The Westchester community is located on 7-plus acres of beautifully landscaped grounds, meticulously maintained with tennis court, 2 heated pools, updated Clubhouse and 3 private Tiki-hut areas. Gulf beaches are what make Longboat Key unique and you can walk for miles on the beach from the condo. Longboat Key also has 10 miles of bicycle paths on either side of Gulf of Mexico Drive. Located just 6 miles from fashionable St. Armands Circle and only a short drive to downtown Sarasota with arts, theatre, restaurants and shopping. This is non-smoking unit. Sorry, this condo association does not allow pets. BOOKED JAN-MAR, 2027.

Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)

Listing Agent: Diann Thelen (941-920-0758)

Remarks: AVAILABLE 9/1/2026 to 12/31/2026. Oceanfront 2 bed/2 bath luxury condo on the 8th floor with beach and golf course views, two private balconies, and resort-style amenities just steps from the sand.The open-concept living and dining area features a custom bar and stylish decor, creating an inviting space to relax or entertain. A dedicated office makes working remotely effortless, while the sleek bar with wine refrigerator is perfect for evening cocktails at home. The fully equipped kitchen with built-in pantry offers everything you need, and the two serene bedrooms with King beds each enjoy convenient access to a full bath.This private, gated resort community offers a true coastal club experience. Host gatherings in the large community room, then move outdoors to the oceanfront pool, jacuzzi, fire pit, and grilling patio. Stay active with a swimming pool, workout room, pickleball, and shuffleboard courts on-site, then stroll directly onto the beach for a swim or sunset walk along the shoreline. 3 MONTH MINIMUM. Rental includes all furniture, appliances, dishes, cookware, and linens. Covered Parking spot #10 included with additional guest parking, seperate storage area for beach/pool items.

Listing is courtesy of: XCELLENCE (866-595-6025)

Listing Agent: Melissa Kontny (863-529-7465)

Remarks: Your winter on the Gulf begins here. This is a rare opportunity to enjoy direct Gulf front living in a fully furnished seasonal residence, available January through March 2027. Tucked behind the private gates of Longboat Key, this premium condo blends the ease of coastal condo living with the comfort of generous, well-designed interiors. Mornings begin with soft sunrise views over the golf course from the bedrooms, while evenings wind down with glowing sunsets over the Gulf from the main living spaces. The primary suite offers walk-in closets and a peaceful retreat, and the open layout creates an effortless flow for entertaining or quiet nights at home. Residents enjoy resort-style amenities including a heated beachfront pool and spa, fitness center, sauna, steam room, and around the clock gated security. Water, cable, Wi Fi, and parking are included, making your stay truly effortless. Located within the Longboat Key Club community, Longboat Key Towers offers a serene beachfront escape while keeping you just minutes from the dining, culture, and lifestyle that make Sarasota so special.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Irma Scherer (941-279-3630)

Remarks: This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The beautiful upgrades to the kitchen and baths go hand in hand with the elegant decor of this property. Fully furnished and fully equipped and ready for your arrival, covered parking for one vehicle and guest parking is available as well. The clubhouse has a full kitchen facility and is large enough for meetings, private parties, and social functions, The exercise room is well equipped with machines and free weights. Classes in water Aerobics are held several times a week during the winter at a nominal cost, Available May to December at OFF Season rate of $4,200 per month plus 13% tourist tax. The property is a NO smoking/NO pet unit.

Listing is courtesy of: REALTY SERVICES INC (941-954-4443)

Listing Agent: Shirley Cuddy (941-321-1549)

Remarks: WILL CONSIDER A 6 TO 12 MONTH LEASE AND WILL FURNISH FOR $7750 PER MONTH. Welcome to Tangerine Bay Club An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5 bath with office/den features views of Sarasota Bay. It is in close proximity to New Pass and the pristine beaches of the Gulf of Mexico. Upgraded Ergon Fall White stone ceramic tile flooring is as beautiful as it is durable. The kitchen will satisfy your culinary desires an features; European cabinetry, lavish corian counters, Ge Profile Stainless steel appliances, Gas cooktop including an 18-bottle wine cooler and double oven. The chef's kitchen desk space will help you plan your extravagant meals. It is conveniently located near the breakfast nook and view of your courtyard. The open floor is illuminated by natural direct and indirect sunlight. Catch breathtaking sunrises over Sarasota Bay or relax by the gas fireplace during the winter. Hang out on the patio enjoying your favorite beverage and enjoy the lush exotic view. Mahogany doors through the residence give the condo a splendid feel. Stay cool all summer long with the brand- new Comfort Maker A/C unit that was just installed. Cleanses and refresh in your spa-like remodeled master bathroom with a new vanity, separate sinks, new toilet, new jacuzzi tub, tile quartz counters, and spacious neutral tile shower. Come enjoy the outrageous serenity of a LBK sunset. Maybe you will be lucky enough to witness a Flash of Green or Bioluminescence lights. Tangerine Bay offers resort-style amenities centered around one of the luxurious private pools on all of Longboat Key. The amenities include a cabana, fitness center, library, hot tub, and pool surrounded by tropical landscape. The resort also features tennis courts, pickleball courts, and a clubhouse. Organized social including group happy hours in the Cabana, scheduled group pickleball games, and planned excursions to local cultural happenings. Come hang out at Your Private Beach Access at Bay Isles Beach Club for only $250 per year. The privacy and island feel of Tangerine Bay is highlighted by its Bay front living enjoy the recently renovated boat dock which is a secret fishing spot or slip into your kayak and launch out for some peace and serene calm. Longboat key is one of the top destinations for enthusiasts of golf, tennis, fine dining, world-class fishing, and boating. In addition, Tangerine Bay Club is positioned at the southernmost point of the island , walking distance to Quick Point Nature Preserve located on the New Pass and Sarasota Bay. Come check out all the tropical birds and enjoy a stroll through the nature path. Bring your fishing pole or picnic lunch. Tangerine Bay is located across from the famous Longboat Key Club Golf Course . Come enjoy fine dining in downtown Sarasota, St Armands Cir, or many highly rated island restaurants. Just over the bridge is City Island, Mote Aquarium, Ken Thompson Park, and Sarasota Sailing Squadron marina. The St. Armand's Circle shopping district and Lido Key Beach are just a few minutes drive.

Listing is courtesy of: SUNREAL ESTATE INC (941-376-7653)

Listing Agent: Karl Helbig (941-376-7653)

Remarks: LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two and a half bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and dryer. The primary bedroom has a king sized bed, on suite bathroom with double sinks and a stall shower, and walk in closet and a ocean view lanai with lounge chairs and table for enjoying the view. The guest bedroom has two twin beds and ocean views from two large windows. Guest bathroom has a stall shower. Front entry is set up as a sitting area with a queen sized murphy bed. The Player Club is abound with amenities. The amenities include a gated entry, beach access, putting green, heated community pool with spa, BBQ grills, tennis, clubhouse, fitness center and large meeting room. No pets allowed. Three month minimum rentals only due to the Association. CALL TODAY. This is not one to miss!!

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: C. Alison Hunter (941-587-5667)

Remarks: AVAILABLE IN JUNE FOR 6-MONTHS OR MORE! Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated elegance. Everything inside is new, from the flooring to the kitchen and baths, the decor is neutral with pops of color, giving the home a coastal urban vibe. The primary bedroom offers a king bed, walk-in closet with built-ins, smart TV and a desk. The primary bath has dual sinks and shower. The guest bedroom boasts queen sleeping accommodations and a smart TV. New luxury vinyl flooring throughout and gorgeous kitchen with stainless appliances, stone counters and lovely wood cabinetry. Outside your door you will find a bonus deck with chaises for sunbathing. This popular, Tim Siebert designed Gulf-to Bay community features 27 lushly landscaped acres, 4 Har-Tru Tennis Courts, a Jr. Olympic pool, kayak launch, bocce ball and fitness room in the clubhouse, and a gorgeous beach, located just across Gulf of Mexico Drive. St. Armands Circle is a short drive away, just over the Ringling Causeway you will find the vibrant downtown Sarasota arts and culture, as well as the many unique shopping and dining venues. Leases less than 6+ months subject to additional taxes and fees.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)

Listing Agent: Stephanie Deshaies (941-780-3229)

Remarks: Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of the gulf. Gorgeous custom kitchen. Granite counters, beautiful muted gray plank flooring. Turnkey furnished with newer linens and a brand new hurricane door off kitchen and dining to master bedroom balcony. Just bring your toothbrush and clothes. Desired location and direct front penthouse sitting right on the Gulf of Mexico w Private beach and chairs and umbrellas for quit time on your beach. The two balconies bring the water to you so you can enjoy a breathtaking sunsets and the unobstructed views everyday. The enormous heated pool and spa, and tennis courts, clubhouse and fitness center. Onsite management from 9 to 4 Monday through Friday. Go over Longboat Key Bridge and take a turn at first stoplight into LONGBOAT KEY RESORT GOLF AND TENNIS CLUB, TELL GATE GAURD AND SAY SHOWING PRIVATEER NORTH AND GO DIRECT TO BUILDING. This complex PRIVATEER NORTH is located furthest South to St. Armand's S0 YOU ARE NOT IN A LOT OF TRAFFIC and minutes to St. Armand's and the mainland.

Listing is courtesy of: CHROME REALTY LLC (941-363-6300)

Listing Agent: Marni Hayden (941-809-5044)

Remarks: AVAILABLE OFF SEASON AND SEASONAL. RENTAL MAY 1, 2026 THROUGH November 30, 2026 AT $5000 A MONTH AND SEASONAL JANUARY 1, 2027 THROUGH APRIL 30, 2027 for $7500. Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor residence. Views from all windows and from the outdoor patio a great view of of the Gulf. Split bedroom plan for privacy. Master bedroom with a king size bed, walk in closet and the all tile bathroom has a convenient walk in shower. 2nd bedroom has a queen comfortable pull out sofa and built in desk area and bathroom tub and shower combination. Large open living area completely tiled with dining table and enjoy all the best of the galley kitchen for easy entertaining. The amenities will complete your time in Paradise in Florida. New clubhouse room with full kitchen. Enormous heated swimming pool and spa, fitness center, sauna, tennis courts, bike storage, pickle ball and have dinner on the beach with outdoor grill area. Restaurants are everywhere along with only minutes to Famous ST. Armand's Circle for great shopping and more of top notch Restaurants. . Walk the 9 mile Beach or ride your bike on Special Longboat Key. Includes internet, electric and cable and more. Turn key furnished. Just pack your bags. Won't last long.

Listing is courtesy of: CHROME REALTY LLC (941-363-6300)

Listing Agent: Marni Hayden (941-809-5044)

Remarks: Available June through December. This first-floor corner condo means extra privacy, added natural light and the convenience of a walk-out patio. Nicely furnished and move-in ready for a comfortable stay. A spacious dining and living area opens out to a screened lanai and large west facing outdoor patio overlooking landscaped grounds. A patio gate allows easy access to a path out to the beach access road plus it makes dog walking a breeze. Yes, Bayport is small pet friendly- a rarity in island condo communities. The primary bedroom has a king bed, large walk-in closet, and an alcove with a desk overlooking the garden. The guest bedroom can be configured as a king or two twins. There is under building parking for one car, outside locked storage and plenty of guest parking. Bayport Beach and Tennis Club is a true Gulf to Bay community, with a fishing pier and kayak launch out to Sarasota Bay, and access to 1200 feet of private beach with beach chairs and umbrellas, just 2-3 minutes from your front door. Enjoy a swim in the Jr Olympic pool, tennis on 4 har-tru courts, a club house, a well equipped gym, and shelled walking paths along tropical landscaped grounds. Groceries, parks and conveniences are within 2 miles, with shopping and terrific dining dotted along the Key. Sarasota's entertainment and cultural attractions are a short drive away.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Rosemarie Mckee (941-504-9396)

Remarks: Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Step inside to find a thoughtfully updated interior featuring modern finishes, a fully equipped kitchen with stainless steel appliances, and a bright, open living and dining area that flows seamlessly onto a private balcony—perfect for morning coffee while watching dolphins play or enjoying spectacular sunsets. The primary bedroom boasts an en-suite bath, while the guest bedroom provides comfort and privacy. Both bedrooms, along with the living room, deliver direct, unobstructed ocean views. This residence comes fully furnished. Additional features include impact-resistant windows and doors, covered parking, and access to the Islander Club’s exceptional amenities: a 24-hour fitness center with Har-Tru tennis courts, an oversized beachfront swimming pool, billiards, a library, and a vibrant community atmosphere just steps from the sugar-sand beach. Located in the heart of Longboat Key on St. Armands Circle and downtown Sarasota, this property offers the perfect blend of coastal luxury and relaxed island living. Whether you're seeking a seasonal rental or a long-term retreat, this oceanfront gem is move-in ready and delivers the best of island living with direct beach access and unforgettable Gulf vistas.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Michele Conn (612-414-7052)

Remarks: Lease/Option - Owner looking to lease up to 6 Months $4300 a Month of Longboat's Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seeds oats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized swimming pool, community area for kayaks, clubhouse, and shuffle board. Longboat Beach Harbor is a friendly community with group events and many fun times to build relationships and enjoy sense of community living. Close to Bayfront Park with Tennis, Publix/CVS shopping. This renovated condo is situated on the 3rd floor not requiring flood insurance. Air conditioned indoor hall-way with electronic security entrance. Newly appointed high grade appliances, bathrooms, HVAC, luxury flooring and trim. Up-scale appointed fixtures and details throughout

Listing is courtesy of: LEN SCAVRON (908-304-5454)

Listing Agent: Len Scavron (908-304-5454)

Remarks: Now available FOR LEASE at The Islander Club on Longboat Key, this updated 2-bedroom, 2-bath residence offers exceptional value in a true beachfront community. Turnkey and move-in ready, the unit features an open layout with quality finishes, an updated kitchen with stainless steel appliances, wood flooring, refreshed bathrooms, and a spacious 38-foot terrace for outdoor living. The primary suite includes an ensuite bath and walk-in closet, while the guest bedroom offers comfort and privacy for visitors. Residents at THE ISLANDER on LONGBOAT KEY enjoy direct BEACHFRONT access along with resort-style amenities including a private beach, heated pool, fitness center, sauna, tennis, pickleball, and on-site management. Offered at $6,000/month May through December and $10,000/month January through April. AVAILABLE NOW for immediate occupancy. Contact listing agent for showing requests. OPEN FOR 2027 SEASON RESERVATIONS - 3 MONTH MINIMUM

Listing is courtesy of: WAGNER REALTY (941-955-1500)

Listing Agent: Richard Ivan (941-800-8891)

Remarks: Offered at $25,500 per month for 3 months in 2027! - Come be on the beach! Rarely available on the south end of Longboat Key, a 3 bedroom + den, 3 1/2 bath DIRECT Beachfront 3-month (90 days total) rental is now available for this coming 2027 winter and spring season. This large 2940 +/- sq ft beachfront retreat is situated on the south side of this building which offers stunning 180-degree beach views along with unobstructed long southerly beach and island views from your front lanai. Tencon on Longboat Key is a true beachfront treasure located directly adjacent to the new St Regis Resort where one can walk right next door to enjoy a wonderful dining experience or sip cocktails on the beach! Situated on 3 beautifully manicured acres with a private gated entrance, gorgeous and recently built resort style pool and spa w covered gazebo area, firepit and tennis court. With only 10 units in this building and just 2 units per floor, each floorplan flows from front to back with a unique indoor-outdoor lifestyle that offers multiple outdoor lanais from each major room. From your semiprivate elevator you enter the residence to an open and bright living room and kitchen dining area with a large wall of windows and sliders while stepping out onto your large front lanai with stunning 180-degree views up and down the beach and coastline. Two nicely sized gracious guest bedrooms are privately situated away from the large owners retreat that includes a luxurious spa like bath w separate soaking tub and shower and dual vanities along with a large walk-in closet. The den/office is located right next to the owner's suite which all provides a wonderful sanctuary away from the main living area. You are located on the desirable south end of Longboat Key where one is a short drive to world famous St Armands Circle w all of its fabulous shops and restaurants or you can pop right over the bridge from St Armands and be right in the heart of downtown Sarasota and all it has to offer. Publix grocery, CVS pharmacy and other shops and restaurants are located on Longboat Key and close by along with city parks and a wonderful biking and walking trail all the way up and down the island. This small intimate complex is private and gated with a secured lobby entrance. With only 10 units in this building this tranquil condominium feels and lives almost like a house on the beach! A hidden treasure for someone who wants to be directly on the beach on Longboat Key this winter or spring. A great value at $25,500 per month in season which includes all utilities. Tenant is responsible for security deposit and all applicable taxes along with a $250 application fee, tenant approval is required by the association.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)

Listing Agent: Carol Aviles (941-356-6777)

Remarks: Absolutely stunning waterfront turnkey furnished rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool, workout room, tennis court, and pickleball. Additionally, it's conveniently located close to Publix, and just a short drive away from St. Armand's Circle, known for its shopping and dining options. This is a wonderful place to live or spend some time enjoying the Florida lifestyle! February - April 2027 is already booked, available now until then.

Listing is courtesy of: ANDRE LECLAIR PROPERTIES LLC (603-234-6480)

Listing Agent: Christian Higgins (772-532-8857)

Remarks: Annual Furnished Rental Available at The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully designed interiors featuring soaring ceilings and expansive floor-to-ceiling sliding glass doors that wrap around the living, dining, and kitchen spaces — framing breathtaking sunrise and sunset views. The gourmet kitchen is a chef’s dream, appointed with Wolf and Sub-Zero appliances, including a six-burner gas cooktop, double ovens, and a paneled side-by-side refrigerator and freezer. The elegant owner’s suite offers a private sanctuary with a spacious walk-in closet featuring custom wardrobe cabinetry, a frameless walk-in shower, and a secluded water closet. A private elevator with keyless entry provides direct access from your private two-car garage into your residence for ultimate convenience and privacy. Nestled within 17 acres of pristine beachfront, The Residences are part of Sarasota’s most exclusive resort enclave. Enjoy unparalleled amenities, including access to St. Regis Butler and Concierge services, a residents-only pool and spa, a private clubhouse, a state-of-the-art fitness center, and beachside cabanas. Just steps away, immerse yourself in the world-class offerings of The St. Regis Longboat Key Resort — from the pristine private beach and family-friendly pools to the unique saltwater lagoon wildlife experience, home to resident Aldabra tortoises. Indulge in rejuvenation at the oceanfront spa featuring vitality pools or delight in one of the resort’s vibrant, chef-driven dining destinations. Experience coastal luxury redefined — The Residences at The St. Regis Longboat Key invite you to live where timeless elegance meets the serenity of the sea.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Jaime Barcelo (941-275-3233)

Remarks: Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous outdoor terrace—ideal for entertaining or simply enjoying the serene waterfront setting. Inside, the chef-inspired kitchen showcases sleek Poggenpohl cabinetry and a full suite of premium Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, microwave, full-size refrigerator, and beverage center. Designed with timeless elegance, the interiors feature curated earth-tone finishes by Marc-Michaels Interior Design. The luxurious owner’s suite offers direct terrace access—perfect for morning coffee with a view—along with a spa-inspired bath complete with dual vanities, soaking tub, oversized glass-enclosed shower, and a Toto bidet water closet. The thoughtfully modified floor plan includes two full bathrooms and comfortably accommodates guests. Set within the exclusive Residences at The St. Regis, this property offers access to over 17 acres of meticulously maintained grounds and 800 feet of pristine Gulf-front shoreline. Residents enjoy an unmatched lifestyle with access to world-class amenities, including personalized butler and concierge services, a renowned spa, in-residence dining, and private resident-only offerings such as a clubhouse, fitness center, pool, spa, and dedicated beach area. Don't miss this rare opportunity to live where others vacation.

Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)

Listing Agent: Jaime Barcelo (941-275-3233)

Remarks: Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the sought-after community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bath residence features all brand-new furnishings and is ideally situated just steps from the marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning bayfront sunrises, with Gulf-side sunsets just a short stroll away. Thoughtfully designed and tastefully furnished, the home offers high-end mattresses dressed in organic cotton linens and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. Residents enjoy access to a private marina with available boat docks and kayak storage, deeded beach access, a heated community pool, shuffleboard courts, and wonderful neighbors. Ideally located just minutes from the upscale dining and boutiques of St. Armands Circle and a short drive to Anna Maria Island, this property offers the perfect blend of tranquility and accessibility. Whether you're boating, fishing, or simply relaxing in the bright Florida room, this is a rare opportunity to experience the Longboat Key lifestyle at its finest. Seasonal rental rates are $6,750/ month in-season and $3950/ month off-season. One tenant must be age 55 or older in accordance with community requirements. Apply now!

Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)

Listing Agent: Geoff Scalera (941-321-4158)

Remarks: LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major updating, with all new designer furniture and furnishings, new custom kitchen and bathrooms. Floor to ceiling glass with panoramic views from every room in the house. MOVE-In and enjoy the Luxury lifestyle and amenities that abound at Grand Bay. GRAND BAY is a 24-hour-manned, GATED community where residents can enjoy two heated swimming pools, hot tub spa, fitness center, tennis, private garage, large clubhouse, many on site activities. Residents can enjoy the Bay Isles Beach Club private beach access to the world famous beach on the Gulf of Mexico. Close to St. Armand's Circle, Downtown Sarasota, and Ana Maria Island. OPEN FOR RESERVATION May through December 2026 for a THREE MONTH or longer stay. There is a 30 day tenant application process with the Grand Bay COA. NO PETS/No Smoking. Additional charges 13% sales/resort tax to be paid by tenants. May through November $7,850. Reservation Confirmed for February through March 2027.

Listing is courtesy of: WAGNER REALTY (941-955-1500)

Listing Agent: Patrice Ivan (941-993-0823)

Remarks: Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the sparkling blue waters of the Gulf of Mexico from rear balcony with access from master bedroom and living room. Master bedroom includes king size bed, walk in shower, & dual sinks. Guest bedroom with two twin beds & a King Bed in the 3rd bedroom. Kitchen includes stainless steel appliances & granite countertops. Side balcony access is from dining room and kitchen with a golf course view! Enjoy the amenities of this luxury condo resort, which includes a fitness center, a tennis court, private beach access, heated pool/spa, a gazebo with complimentary grills, 24 concierge/security, and within a golf course community. Rent includes water, sewer, basic cable, and internet. Electric will be a shared expense. Call now for more details!

Listing is courtesy of: ROSSI & COMPANY INC (941-955-7368)

Listing Agent: Deserea Hardy (941-960-6480)

Remarks: AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find a bright and inviting floor plan featuring a well-equipped kitchen, spacious living area, and a private bedroom suite designed for relaxation. The unit includes the added convenience of an in-unit washer and dryer, making extended stays effortless. Enjoy your morning coffee or evening unwind with a Gulf view, while being just moments from the community’s private beach access—only a short walk across Gulf of Mexico Drive. Beach Harbor Club offers resort-style amenities including: Large heated community pool Fitness center Clubhouse for social gatherings Marina and bayfront dock access Community grills and outdoor seating areas Covered parking and bike storage Located in the heart of Longboat Key, you are minutes from Publix, CVS, St. Armands Circle, downtown Sarasota, and Anna Maria Island, giving you easy access to dining, shopping, and entertainment while still enjoying a peaceful beachside setting. Non-smoking unit No pets allowed. Sate and local tourism tax applies to any lease 6 months or less, along with application fees, and $250 cleaning fee.**

Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)

Listing Agent: Brigette Marcus (941-315-9500)

Remarks: ELEGANT BEACH FRONT CONDO ON LONGBOAT KEY. This exquisite 2 bedroom, 2 bathroom condo has been totally updated. The kitchen has top of the line, state of the art appliances. Induction stove top, touchless kitchen sink faucet, cooking island, breakfast bar. From the moment you enter this property you are greeted with a wide open floor plan. Incredible views of the Gulf of Mexico and Sarasota Bay. Tastefully decorated with flowing neutral tones. This corner unit offers views from every room with Floor-To-Ceiling windows and remote control window treatments. There are many amenities in this beautifully maintained building. They include Climate Controlled Bicycle Room and Kayak Storage, Gulf Front Heated Pool, Har-Tru Tennis Courts, Fitness Room, Social Room and Conference Room all for your use. Walking distance to Publix Market and minutes to St Armand's Circle and Downtown Sarasota for boutique shopping, Fine and Casual Dining and our renowned Theater District. Don't hesitate to make this your next vacation spot. This property is available beginning 12/04/2025. Building requires a 2 months minimum rental. LUXURY VACATION RENTAL, LONGBOAT KEY, GULF OF MEXICO, SARASOTA VACATION RENTAL.

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: Teresa Ribaudo (941-376-4500)

Remarks: FURNISHED CONDO ON THE BEACH ! AVAILABLE MAY 1ST! SORRY JAN 1- MARCH 2027 IS NOT AVAILABLE . May - November are AVAILABLE MONTHS. This wonderful Condo 2 bed/2 bath and den is now available. Beach Place is one of the most sought out places on Longboat Key. Located mid-island, this association has a FANTASTIC beach, large heated pool, spa and his/hers fitness areas, EV charging station, tennis, pickle ball, and MORE!This condo is on the first floor so it has it's own entry so you don't have to use the elevator. The condo is completely turn key with pool toys and everything. All you need is your toothbrush and a bathing suit! The master bedroom overlooks the center lake and you do have a peek at the ocean. The 2nd bedroom has twin beds and the den has a pull out couch. All of the rooms have tv's. Enjoy coffee or cocktails on the porch for sunrises/sunsets! Utilities, good wifi and basic cable come with the unit. (cap on electric ). Sorry no pets per association. Resort taxes and cleaning fee not included. Come get out of the cold and put your toes in the sands of Longboat Key!! ( sorry porch furniture is in the living room because the balcony is getting painted!)

Listing is courtesy of: STOCKTON REALTY ADVISORS LLC (941-365-2221)

Listing Agent: Annabelle Newland (231-883-7402)

Remarks: Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and convenience—ideal for both long-term living or a seasonal retreat. Inside, you’ll find soaring high ceilings and a bright, open layout highlighted by a stunning floating staircase and the added convenience of a private elevator, providing effortless access to every level of the home. All-new furnishings and thoughtfully selected artwork create a refined yet relaxed island feel throughout. Designed for both comfort and entertaining, the home features four TVs—including one on the screened patio—WiFi included, and a fully equipped kitchen complete with a wine refrigerator, Nespresso and Keurig machines, and everything needed from cookware to linens for a seamless, turnkey experience. The spacious primary suite offers a true spa-like retreat with a large custom bathroom, double vanities, and a separate walk-in shower. An attached garage adds everyday convenience, while the thoughtful layout ensures both comfort and functionality. Outdoor living is where this home truly stands out. Enjoy a large screened deck with sweeping views of Hole 4 and a tranquil water backdrop, creating the perfect setting for morning coffee, outdoor dining, or relaxing evenings. A dedicated BBQ deck just off the kitchen makes entertaining effortless, while just steps away you’ll find a heated pool and large hot tub, offering a true resort-style extension of your living space. One of the most sought-after features of this home is exclusive access to the private Bay Isles Beach Club. This gated, resident-only beachfront retreat offers a rare level of privacy and comfort on Longboat Key. Enjoy pristine Gulf-front beaches, convenient parking, shaded picnic areas, pavilions, and a relaxed, uncrowded atmosphere that feels worlds away from public beach access. Whether you're enjoying a full day at the beach or catching sunset over the Gulf, this private club experience truly sets the property apart. Located behind the 24/7 manned gates of Bay Isles, this home also places you close to everything you need—Publix, dining, EMS services, and miles of scenic walking and biking paths near the golf course and harbor. Just minutes away, you’ll find the vibrant energy of St. Armands Circle, the luxury of the St. Regis, and the laid-back charm of Anna Maria Island. Available as a 12-month rental or seasonal lease with a minimum 3-month stay, this is a rare opportunity to enjoy turnkey island living with true resort-style amenities in one of Longboat Key’s most desirable communities.

Listing is courtesy of: SECURE DOOR PROPERTY MANAGEMENT (941-231-4065)

Listing Agent: Andrew Clark (941-929-4223)

Remarks: Available January - April 15 Call for rates and availability. Prefer three month lease. Tremendous view of the Gulf from this Gulfside/Beachside 2 BR/2 B condo. Direct Gulf front unit. Breathtaking view of the pristine waters of the Gulf of Mexico. Sit on the balcony to your 7th floor unit. Take in the sunsets with your loved ones and friends. Just a couple minutes and you'll be walking on the fine sandy beach. Go for a swim in the heated pool or the invigorating Gulf waters. Close to St. Armand Circle and Downtown Sarasota. Enjoy the best that Longboat Key offers. Condo application fee required

Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)

Listing Agent: William Glade (941-356-1054)

Remarks: DIRECTLY on the GULF. WITH PRIVATE BEACH .Be Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ocean view throughout its open floor plan that is visible from the time you walk in the door, through the beautiful dining area, upscale kitchen, and tranquil living area. The primary King suite features an elegant walk-in shower and double vanity, along with a guest closet that will provide everything you need for a peaceful night’s sleep. A spacious queen guest bedroom next to the second bathroom, and a cozy third bedroom designed around a queen bed with a twin bunk perfect for additional guests. This unit in a hard to find 8-unit complex with breathtaking Gulf views, a private beach access located on the North end gives you the best of what the Key has to offer, privacy, amazing restaurants throughout Longboat, relaxing beach walks, unforgettable sunsets, a short stroll to many nearby restaurants and is centrally located; only 8 miles north from the renowned St. Armond’s Circle known for its outstanding restaurants and shopping scene, and 8 miles south of Anna Maria Island, known for its good eats, live music and fun atmosphere. Call for rates and availability.

Listing is courtesy of: WILLIAM GLADE LIC. REAL ESTATE BROKER (941-356-1054)

Listing Agent: William Glade (941-356-1054)

Remarks: STUNNING GULF VIEWS! Enjoy the sparkling glimmer of the morning waters and picturesque sunsets from almost every room. This meticulously maintained 2 bedroom, 2 bathroom furnished condominium features an open concept floor plan with expansive Living/Dining/Kitchen area. The generous size primary bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a desk. Bayport Beach & Tennis Club is an amenity-rich community at sea's edge with 27 acres of lush mature tropical landscaping. This gulf to bay community offers an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Just minutes to St. Armand's Circle which is well known for its world class shopping and dining. Cross over the Ringling Bridge to Downtown Sarasota where you will find additional dining, theater, opera, ballet, symphony, art galleries, the Van Wezel Performing Arts Hall, Selby Gardens and of course the Ringling Museum. NOW AVAILABLE MAY - DECEMBER 2026 - OFF SEASON RATE APPLY - CALL FOR AVAILABILITY.

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Antonietta Car (813-684-9500)

Remarks: **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly on the beach, offering you breathtaking full views of the shimmering turquoise waters, sparkling sand, and those iconic Florida sunsets. This is the perfect opportunity to immerse yourself in the serenity of beachfront living during the best time of year. Imagine waking up each morning to the calming sound of waves and enjoying your morning coffee on the balcony as the sun rises over the Gulf. Step inside and be welcomed by the calm coastal colors and casual elegance that make this condo the ideal beach retreat. The community of Arbomar offers amenities that ensure your stay is as relaxing as possible. Take a dip in the heated community pool, stay active in the fitness room, or gather with friends in the community kitchen and lounge. Additional conveniences include climate-controlled storage lockers, a kayak rack, beach chair storage, and laundry rooms on each floor. With all-new Miami Dade certified high-impact windows, including turtle-tinted beachside windows to protect our local sea turtles, you can enjoy the view and feel secure. This spectacular Penthouse condo emphasizes the exclusivity and appeal of spending winter in a beachfront condo.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Norma Mladineo (941-363-1588)

Remarks: Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel appliances. The dining area offers seating for four, there is a wet bar with beverage chiller for convenience. The living room offers comfortable seating, a flat screen TV and amazing water views! The primary bedroom has a king bed, amazing views, a flat screen TV, and a walk-in closet. The primary bath offers dual sinks and a walk-in shower. The guest bedroom has a King bed and Flat screen TV for streaming. You will love this wonderful location, with shopping and dining close by, and Historic St. Armands Circle is just a short drive away. Welcome to Paradise! (All rates are plus taxes and fees) (Booked May through the end of November, 2026 and booked January and February of 2027)

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL (239-262-4242)

Listing Agent: Stephanie Deshaies (941-780-3229)

Remarks: Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease. Groceries are carried in with ease, morning coffee is enjoyed on your lanai, and just beyond, a nearly private lawn stretches out like your own backyard retreat. Only sixty feet away, the tranquil waters of Cranes Bayou create a breathtaking backdrop along with the Sarasota Bay. From your windows and lanai, the view feels intimate and serene as dolphins surface in the distance, manatees glide through calm waters, and coastal birds fill the sky. Just outside, an eagle’s nest tucked within a Spanish pine offers a daily reminder that nature is not something you visit here; it’s something you live beside. The lifestyle extends beyond the view. A deeded private walkway leads you directly to the soft sands of the beach, inviting spontaneous sunset strolls, morning shell hunts, and afternoons spent with your toes in the sand. For boaters, a private slip just steps from your front door makes life on the water feel effortless, ready for quiet cruises or sunset rides along the coast. Recently refreshed with a 2025 community pool upgrade and lush landscaping, the setting feels nature-filled with peacefulness. Inside, the residence reflects a thoughtful balance of high-end furnishings, warm textures, and a blend of contemporary design and classic Old-Florida charm, creating a space that feels both elevated and inviting. Carefully curated lighting, including modern fixtures and Frank Lloyd Wright–inspired sconces, lets you shape the atmosphere, whether you're hosting friends, unwinding with a book, or enjoying a quiet evening at home. This is more than a seasonal escape; it’s a place where mornings feel slower, evenings feel softer, and everyday moments carry the calm of island living. For those looking for a coastal rental that blends privacy, tranquility, and a seamless connection to the water, this inviting retreat delivers an island lifestyle you’ll appreciate the moment you step inside. ANNUAL RATE $4,000 / month. SEASONAL RATE $6,500 / month.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: John Schafer, V (954-298-6229)

Remarks: Available for season 2027! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by the heated pool, gather at picnic areas and cabanas with grills, or explore the water with provided kayaks. Residents also enjoy a newly renovated clubhouse with library and card & game room and state-of-the-art fitness center. In addition to that, get crafty at the wood workshop (all tools included). This ground floor condo has room to sleep six with three queen size beds. The kitchen is fully equipped with everything you need to prepare meals. There is ample seating for dining and gathering space. In addition to our renowned beaches, Sarasota and Manatee county boasts a vibrant cultural scene, with live theater, concerts, ballet, opera, galleries, museums, and even a rich history with the circus arts! Escape the winter and come enjoy Florida living on Longboat Key.

Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)

Listing Agent: Maureen Plichta (941-812-5799)

Remarks: Stunning Portobello Vacation 2/2 Condo on Longboat Key. Season rate is $8000 (Jan-Apr) and off season rate is $5500 (May-Dec). Minimum 2 month rental and full months only. This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style décor, new windows and sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes and HD Extreme channel lineup, king size Master bed and guest bedroom provides two double beds, in unit washer and dryer for convenience. One assigned parking space and guest parking available for second car. Wi-Fi and cable package are provided. Heated swimming pool, tennis court and boat dock located conveniently across the street on the bayside of the complex. Only 1/2 mile to Publix shopping and dining center and approximately 5 miles from fabulous St. Armand's Circle. Sorry no pets permitted (no exceptions). No smoking permitted. 13% sales and tourism taxes apply for any rental less than 6 months. Property is available Apr 2025-Dec 2026 and Apr 2027 and after.

Listing is courtesy of: LINDSAY LEASING LLC (941-404-8878)

Listing Agent: Terri Lindsay (941-404-8878)

Remarks: ABSOLUTELY GORGEOUS INSIDE! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to private beach on the Gulf of Mexico for morning beachcombing, surf casting or memorable sunsets. NOW AVAILABLE: July through December 2026 - OFF SEASON RATES NOW APPLY. Please contact Agent for availability.

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Antonietta Car (813-684-9500)