Location: Longboat Key
Do Not Show Listings
LONGBOAT KEY, FL 34228
$6,0001100 Days on yellowkey MLS ID: A4572396
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1977Community: Seaplace IiiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
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)
730 FOX ST, LONGBOAT KEY, FL 34228
$5,500135 Days on yellowkey MLS ID: A4679347
REDUCED by $1,000 (15.4%) on 05/25/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1350 Built: 1965Community: Longbeach On Longboat KeySingle Family
Remarks: Serene and cozy home in beautiful Longboat Key Village, place where the old Florida meet the new one. Exquisite dining is couple minutes away (The Shore, Whitney’s or Mar Vista), as well as almost private Whitney Beach. Old times charm slows the time itself and once you enter the home, you will feel like on vacation. Three bedrooms, three bathrooms (two of them are en-suite), nice living room with dining are and spacious kitchen will make you feel at home right away. The kitchen is fully equipped for your convenience. Outdoors of this home is even more welcoming and paradise-life. Lush and tropical garden around the beautiful swimming pool, cabana with comfortable seating or other seating areas are there just for our guests. There is plentiful parking spaces in front of the house or next to it. And - the beaches..yes that is what matters. Whitney Beach on Longboat Key, couple minutes of walk. Or you can visit the Beer Can Island, popular place for boats to hang out. Coquina Beach on Anna Maria Island is not far also. La Paloma just has it all! Sweet home with good vibe close to all you need on vacation!
Listing is courtesy of: ENVISION REALTY PARTNERS LLC (941-840-3188)
Listing Agent: Linda Votrubova (941-840-3188)
2425 GULF OF MEXICO DR #7C, LONGBOAT KEY, FL 34228
$12,0002984 Days on yellowkey MLS ID: A4215382
INCREASED by $1,000 (9.1%) on 05/25/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $7,896 (2021)Community: Sea Gate ClubSpa: YesCondo
Taxes:$7,896
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2021
Middle School: Booker Middle
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)
603 LONGBOAT CLUB RD #204N, LONGBOAT KEY, FL 34228
$12,00077 Days on yellowkey MLS ID: A4686763
0 Days Off yellowkey (back on 5/23/2026)
REDUCED by $3,000 (20.0%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1560 Built: 1970Community: Longboat Key TowersSpa: YesCondo
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)
4825 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$7,800400 Days on yellowkey MLS ID: A4651021
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Community: Westchester Condo Apts Un 3Condo
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.
6979 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$10,000312 Days on yellowkey MLS ID: A4660175
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1454 Built: 1974Community: Longbeach On Longboat KeySingle Family
Remarks: Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room includes bunk beds for family fun. Accommodating up to 9 guests, the property is just a short stroll to pristine Whitney Beach and nearby fishing docks, with top local restaurants and cafes — like Mar Vista, Shore, Whitney’s, and more — only minutes away. A local owner ensures attentive service to make your stay unforgettable. $10,000 off season/$14,000 season.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Rinat Sikdar (941-993-9292)
1050 LONGBOAT CLUB RD #803, LONGBOAT KEY, FL 34228
$6,00017 Days on yellowkey MLS ID: L4961980
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1974Community: Privateer NorthSpa: YesCondo
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)
3210 BAYOU SOUND, LONGBOAT KEY, FL 34228
$7,50020 Days on yellowkey MLS ID: A4693846
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2091 Built: 1978Community: Bay IslesSpa: NoSingle Family
Remarks: Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered turnkey furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms plus an office, updated bathrooms, a spacious kitchen with premium appliances, and multiple indoor-outdoor living spaces designed for relaxed island living. Enjoy a private lap pool, screened upper-level deck, tropical landscaping, and a rare 3-car garage. Residents also have access to the exclusive BAY ISLE BEACH CLUB with private Gulf beach access. Publix, St. Armands Circle, and downtown Sarasota are all just minutes away. Available immediately for occupancy. Rates are $7,500/month May through December and $14,500/month January through April. 3 MONTH MINIMUM - Contact listing agent for availability and showing requests.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Richard Ivan (941-800-8891)
909 SPANISH DR N, LONGBOAT KEY, FL 34228
$2,95015 Days on yellowkey MLS ID: A4694346
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1300 Built: 1969Community: Spanish Main Yacht ClubSpa: NoVilla
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features neutral tile plank flooring throughout, a spacious chef’s kitchen with 42-inch wood cabinets, quartz island that seats seven, slow-close drawers, and new appliances—all opening to a bright living area. The primary suite offers an en-suite bath with frameless glass shower and double sinks, plus a large walk-in closet. Step through new double doors to a generous screened lanai overlooking lush wetlands and Bay views, perfect for relaxing, dining, or using as a flexible third space, complete with retractable awning, brick paver patio, hurricane-rated windows and doors, motion lights, and electric blinds. In the vibrant 55+ Spanish Main Yacht Club community enjoy a pool, shuffleboard, private deeded beach access on Longboat Key, and easy boating, fishing, and cycling, all just minutes from St. Armands Circle, downtown Sarasota, dining, shopping, and the airport. Basic cable and water included. Move-in ready and waiting—call for details on this piece of paradise.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
Listing Agent: Alex Lane (941-960-3080)
613 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$17,500330 Days on yellowkey MLS ID: A4655401
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1871 Built: 1967Community: Longboat Shores RevSpa: YesSingle Family
Remarks: Available for season 2027 Looking for a 3 month rental. Newly renovated, this beautiful home features a split floor plan with generously sized bedrooms and walk-in closets, all enhanced by a charming coastal flair. The kitchen—truly the heart of the home—is fully equipped with everything you need to prepare delicious home-cooked meals. Enjoy your morning coffee or an evening cocktail in the cozy coffee-bar area. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into the crystal clear deep end. Plenty of new stone pool deck on the offered lounge chairs to bask in the Florida sun. Welcome to peaceful Buttonwood Harbour, composed of 50 homes in one of Longboat Key's oldest and sought-after communities. Situated in the middle of Longboat Key, it is walking distance for most, to Publix, the Shoppes of Bay Isles, Tennis, post office, and CVS. Full of friendly neighbors and a favorite place for nature lovers. Boaters and fisherman will be happy with accessibility to the BHA boat ramp for launching and ability to dock your boat at the house during your stay, even utilize the kayak storage if you decide to rent them. No bridges from Buttonwood Harbour out to Sarasota Bay's open waters. Enjoy the day at Bayfront Park, 1.4 miles from the house. Amenities found at Bayfront Park include a 1,350 square foot indoor Recreation Center, a playground, a basketball court, shuffleboard courts, a multi-purpose open field, 3 dedicated pickleball courts, a tennis court, picnic tables, restrooms, and parking for a Town public beach access located across the street. The Bayfront Park Recreation Center is a public recreation facility run by the Town of Longboat Key. You will also find a dog park for your fur babies.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
601 LONGBOAT CLUB RD #902S, LONGBOAT KEY, FL 34228
$9,000177 Days on yellowkey MLS ID: A4674604
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1970Community: Longboat Key TowersSpa: YesCondo
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)
2319 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$12,5003701 Days on yellowkey MLS ID: A4151865
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2532 Built: 1986 Tax: $8,895 (2021)Community: Harbour OaksSingle Family
Taxes:$8,895
Remarks: SEASONAL: All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedroom, 2 1/2 bath home overlooks the Longboat Key Club golf course! With over 2,500 sq. feet of living space, pool, private Beach Club access and sought after Southern Longboat address this is the perfect Winter getaway. One visit to this 3BD+Den/2.5BA golf course detached home will have you wanting more! It has been updated in all the newest tones, is fresh, and combined with natural lighting, is so inviting. Pavered drive and lush landscaping and walkway lead you into the foyer entry. The combined living/ dining area is warm and inviting with vaulted ceilings, tile flooring and new comfortable furnishings. The kitchen is designed for entertaining or just relaxing with a marvelous view of the 2nd green. The den is a cozy retreat for TV or for catching up on work or emails in the dinette area. The private and spacious master suite offers ensuite bath and has a seating area to relax and enjoy the views! The second bedroom features queen accommodations and the third bedroom offers twins. All have their own private entrance for a relaxing stay. Additional charges for pool heater use. This marvelous turnkey residence comes complete with gated security, Wifi, inside laundry, 2 car garage, private and community pool and easy access to shopping, dining and cultural arts from St. Armands Circle to downtown Sarasota. Booked Jan - April 2027.
360 GULF OF MEXICO DR #312, LONGBOAT KEY, FL 34228
$6,00071 Days on yellowkey MLS ID: A4687695
REDUCED by $500 (7.7%) on 04/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2298 Built: 1992Community: Tangerine Bay ClubSpa: NoCondo
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)
1485 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228
$11,0001354 Days on yellowkey MLS ID: A4548403
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1839 Built: 1981Community: Players Club ISpa: NoCondo
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 Agent: C. Alison Hunter (941-587-5667)
750 BAYPORT WAY #750, LONGBOAT KEY, FL 34228
$4,2501431 Days on yellowkey MLS ID: A4540609
REDUCED by $750 (15.0%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1983Community: Bayport Bch & Ten Ph DCondo
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)
1050 LONGBOAT CLUB RD #1006, LONGBOAT KEY, FL 34228
$6,0001299 Days on yellowkey MLS ID: A4552081
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)
1050 LONGBOAT CLUB RD #804, LONGBOAT KEY, FL 34228
$5,0001137 Days on yellowkey MLS ID: A4567693
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972Community: Privateer NorthSpa: YesCondo
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.
2301 GULF OF MEXICO DR #102N, LONGBOAT KEY, FL 34228
$16,00035 Days on yellowkey MLS ID: A4692071
INCREASED by $7,000 (77.8%) on 05/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970Community: Islander Club Of LongboatSpa: YesCondo
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)
4780 GULF OF MEXICO DR. VILLA 5, LONGBOAT KEY, FL 34228
$7,000231 Days on yellowkey MLS ID: A4668115
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1974Community: Windward Bay AmdVilla
Remarks: Booking Now for Summer 2027! Booked for January-June 30, 2027. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$4,30050 Days on yellowkey MLS ID: R4911069
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Community: Beach Harbor ClubSpa: NoCondo
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)
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