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: STUNNING BAY VIEWS! Enjoy picturesque sunrises from your private deck in this tastefully decorated 2 bedroom, 2 bathroom furnished condominium. This home has an open concept floor plan which features an expansive Living/Dining/Kitchen area. The generous size master 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. Please call for availability. OFF SEASON RENTAL ONLY - AVAILABLE : MAY - DECEMBER 2026. Please call Agent for availability.

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

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

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: Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the stylish seating, dining! The master suite offers wonderful Gulf views and access to the open patio, a king bed, flat screen TV, and walk-in closet. The master bath has dual sinks, soaking tub and an oversize shower. The guest bedroom offers two twin beds, flat screen TV, and views of the lushly landscaped grounds and views of the bay. In unit washer and dryer. This is one of the most sought-after buildings on Longboat Key, this well managed community was recently renovated with elegantly redecorated lobby and corridors, along with two social rooms, the Sunrise and Sunset rooms. There are Men's and Women's workout rooms, four Har-Tru tennis courts, two outdoor gazebos with gas grills and seating, a gorgeous gulf side heated resort style pool and spa, all surrounded by meticulously maintained grounds. Take the walkway to the sparkling sands of the private beach where there are plenty of chairs and chaises to relax and restore! The community offers 24/7 security and concierge services, and on-site management. Wake up, and fall asleep to, the sound of the waves gently lapping the shore. Welcome to Paradise!

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

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

Remarks: Call for rates and availability .Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck directly onto the beach? Stay in this 3 bedroom (2 king beds/1 queen), 2 bath condo in Salty Acres with 2 covered parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and recently remodeled. It must be a monthly rental. $5,500 a month April - October. $5,750 November, $5,500December, $7,000 January, $8,000 February, $9,000 March $12,000

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

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

Remarks: Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Primary Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive white sand beach on the Gulf of Mexico.

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

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

Remarks: Pristine Gulf Beachfront on Longboat Key Welcome to this beautifully updated 2-bedroom, 2-bathroom luxury beachside retreat located in The Shore on mid-Longboat Key. This inviting second-floor condo offers stunning Gulf views and is just steps from the powdery white sand and crystal-clear waters—an ideal setting for a relaxed island getaway. Highlights -Sweeping Gulf views from living room and master bedroom -Thoughtfully remodeled with an airy, open-concept layout and generous living spaces -Modern kitchen featuring granite countertops and a spacious island, perfect for dining and entertaining -Fully furnished and well-appointed for a turnkey, stress-free stay -Breathtaking Gulf views from the main living area, showcasing unforgettable sunrises and sunsets Configuration - Primary Bedroom: King bed - Walk-in closet - En-suite bathroom with double sinks and walk-in shower - Direct access to the patio for refreshing Gulf breezes - Second Bedroom - Two Queen-size beds Additional Conveniences & Amenities - In-unit washer and dryer - Watch dolphins, manatees, turtles, birds, and passing boats right from your retreat - Beachside heated pool and hot tub - Fitness center and sauna - Large social room with catering kitchen - 1 Covered parking spot, plus guest parking - Bicycle and kayak storage - Beautifully maintained grounds with lush tropical landscaping and mature trees - Weber grill on your private patio - perfect for cooking and dining while taking in breathtaking Gulf views Note: 60-Day Minimum Rental (January through April are not available) Please call or text listing agent for questions or showings 2nd Floor Unit - Elevator and/or stairs available Association Application Required No Pets

Listing is courtesy of: DARAK GROUP INCORPORATED (704-430-1670)

Listing Agent: Matt Darak (704-430-1670)

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: BRING YOUR BOAT, deeded private boat slip that accommodates up to a 60 ft boat INCLUDED! Picturesque Waterview of Sarasota Bay and easy access by boat to the Gulf. Recently renovated with high end appliances, finishes and designer furniture. The Harbor Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boat ramp, kayak launch/storage, 3 tennis/pickle ball courts, covered parking and 400' of boat slips and bayfront. This unit features 2 assigned covered parking spaces, over 1500 sq ft of living space in this end unit, high ceilings, water views in all rooms, open floor plan, large, enclosed balcony off living/dining room plus separate balconies off each bedroom, washer/dryer and extra-large bathrooms. High Speed Wi-Fi, SMART TV's with cable and utilities included. Seasonal rental for select times of the year ONLY. 10-day notice required along with application for owner approval. Weekly rentals available with owner approval January 7-April 15

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

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

Remarks: Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a modern, chic design, featuring plush seating, rich textures, and sophisticated décor. The gourmet kitchen is fully equipped with top-of-the-line stone countertops, custom cabinetry, and state-of-the-art appliances. The elegant bedroom includes a king-sized bed with luxurious linens, soft lighting, and unique, custom-made furniture. 2 modern bathrooms- one half bathroom for guests and a full bathroom off of the master bedroom that includes high-end finishes, a freestanding soaking tub, a spacious walk-in shower, double vanities, and a calming color palette. The unit also offers a sound system, parking in the private garage and full laundry room. The Resort has plenty of amenities for everyone to enjoy. Enjoy first class dining, an underwater sea lagoon or a lazy river float after drinks at the Monkey Bar. The Resort also offers a spa, coffee shops, butler service, event planning, fitness center, private cabanas and much, much more.

Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)

Listing Agent: Larry Starr (941-914-6869)

Remarks: 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. Inquire about 6 and 9 month pricing.

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

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

Remarks: Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The Large primary bedroom has a King bed and bathroom with a walk-in shower with his/her sinks and a separate seating area. A privacy door has been added from the Master bedroom to the en-suite bathroom. The unit comes with a large utility closet for ample storage and a stackable washer and dryer in the kitchen. Guest Bedroom has 2 twin beds and an adjoining bathroom. Amenities include a 24 hour manned guard gate, private beach access, Wi-Fi, lighted tennis courts, pickleball, heated pool and hot tub, two state of the art fitness centers, and BBQ gas grills by the pool. This condo comes with 2 parking spaces - one inside the building close to the elevator and the other outside. Minutes to St. Armand's Circle for first class shopping and dining. Off-season guests pay the monthly electric bill. Sorry, no pets or smoking permitted.

Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)

Listing Agent: Margaret Young (941-359-3435)

Remarks: Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat screen TV's, wireless internet and in-unit washer and dryer. Amenities abound at Beachplace including a junior-sized Olympic pool, kiddie pool, spa, tennis courts, grilling areas, clubhouse, and fitness center. Walkers or joggers will love the lush landscaping and extensive (1450 lineal feet) private beach. St. Armand's Circle's shops and restaurants is less than a 5 minute drive and downtown Sarasota with its arts and culture is less than a 15 minute drive. If you simply want to relax, beach umbrellas and chairs are laid out daily for your relaxation. Simply enjoy! No pets or smoking allowed.Booked Jan- Apr, 2026. Available June, August, September, October and December, 2026.

Listing is courtesy of: Gulf Coast Rental Homes&Condos (941-212-1972)

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