$6,000 per month
706 Bayport Way Unit 706, Longboat Key, FL 34228
706 Bayport Way Unit 706, Longboat Key, FL 34228
$10,000 per month
522 Bayport Way Unit 522, Longboat Key, FL 34228
522 Bayport Way Unit 522, Longboat Key, FL 34228
$9,500 per month
519 Bayport Way Unit 519, Longboat Key, FL 34228
519 Bayport Way Unit 519, Longboat Key, FL 34228
$10,000 per month
720 Bayport Way Unit 720, Longboat Key, FL 34228
720 Bayport Way Unit 720, Longboat Key, FL 34228
$9,500 per month
744 Bayport Way Unit 744, Longboat Key, FL 34228
744 Bayport Way Unit 744, Longboat Key, FL 34228
$9,500 per month
517 Bayport Way Unit 517, Longboat Key, FL 34228
517 Bayport Way Unit 517, Longboat Key, FL 34228
$10,000 per month
832 Bayport Way Unit 832, Longboat Key, FL 34228
832 Bayport Way Unit 832, Longboat Key, FL 34228
$11,000 per month
739 Bayport Way Unit 739, Longboat Key, FL 34228
739 Bayport Way Unit 739, Longboat Key, FL 34228
$10,000 per month
523 Bayport Way Unit 523, Longboat Key, FL 34228
523 Bayport Way Unit 523, Longboat Key, FL 34228
$10,000 per month
838 Bayport Way Unit 838, Longboat Key, FL 34228
838 Bayport Way Unit 838, Longboat Key, FL 34228
$6,000 per month
817 Bayport Way Unit 817, Longboat Key, FL 34228
817 Bayport Way Unit 817, Longboat Key, FL 34228
$3,200 per month
600 Sutton Place Unit 201, Longboat Key, FL 34228
600 Sutton Place Unit 201, Longboat Key, FL 34228
$9,000 per month
830 Bayport Way Unit 830, Longboat Key, FL 34228
830 Bayport Way Unit 830, Longboat Key, FL 34228
$10,000 per month
741 Bayport Way Unit 741, Longboat Key, FL 34228
741 Bayport Way Unit 741, Longboat Key, FL 34228
$9,000 per month
833 Bayport Way Unit 833, Longboat Key, FL 34228
833 Bayport Way Unit 833, Longboat Key, FL 34228
$10,000 per month
805 Bayport Way Unit 805, Longboat Key, FL 34228
805 Bayport Way Unit 805, Longboat Key, FL 34228
$13,500 per month
716 Bayport Way Unit 716, Longboat Key, FL 34228
716 Bayport Way Unit 716, Longboat Key, FL 34228
$4,900 per month
561 Tarawitt Dr, Longboat Key, FL 34228
Bring your boat and walk to the beach from this beautiful 2 bedroom/2 bath home that sits on a canal to the intercoastal. There is a dock and plenty of seawall with 2 whips on this double lot home for other water toys as well. The home has just had a kitchen renovation with brand new cabinets and appliances. With 1800 square feet inside, there is room to spread out. The back of the property has
$6,900 per month
535 Forest Way, Longboat Key, FL 34228
Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step into
Andy Moore GULF COAST REALTY & MANAGEMENT
$6,750 per month
600 Sutton Plaza Unit PH 402, Longboat Key, FL 34228
Every morning waking up and seeing the beautiful Sarasota bay. Watching manatees and dolphins playing in the water. And beach access directly across the street. We already have so many very fond memories of this place that we wish to share with others. Thank you for your consideration.
$4,550 per month
Unlisted Address
Merging classic elegance with modern luxury featuring high vaulted ceilings, a state-of-the-art kitchen, high-speed internet, and a cutting-edge reverse osmosis water system. Enjoy the convenience of an in-closet washer/dryer and UV air filtration for pristine air quality. Perfect for romantic getaways or peaceful solitude, with boat parking & public launch nearby. The property offers a furnished
Keith Gordon GETMOREOFFERS
$9,850 per month
701 Broadway St, Longboat Key, FL 34228
Newly remodeled bungalow blocks from Whitney Beach & a block from bay. Historic home was once a post office in the 1920's. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! Sleep tight in a quiet neighborhood that allows zero public parking. Very serene, private
Keith Gordon GETMOREOFFERS
$10,000 per month
380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
Available now through the end of the year, off season only. Welcome to coastal elegance at Tangerine Bay Club, where sweeping bay views set the stage for an exceptional lifestyle. This furnished residence captures the charm of a single-family home with its private courtyard entrance while offering all the benefits of resort-style community living. This comfortable three-bedroom retreat features a
Maureen Plichta STRINGER MANAGEMENT INC
$25,000 per month
1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
Welcome Serenity Oasis, your paradise at The Residences at the St.?Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat.The expansive living room is
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$7,800 per month
4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$45,000 per month
2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
Step into unparalleled elegance with this stunning 4-bedroom, 4.5-bathroom beachfront condo, where modern sophistication meets coastal serenity. This exclusive residence boasts floor-to-ceiling windows that fill the space with natural light and showcase breathtaking panoramic Gulf views from every angle. Designed for ultimate privacy and comfort, the unit features direct elevator access, a
Larry Starr SVN COMMERCIAL ADVISORY GROUP
$8,000 per month
3010 Grand Bay Blvd Unit 445, Longboat Key, FL 34228
Welcome to Grand Bay on Longboat Key! Your private elevator will take you directly to your unique double-door entry. Once you are inside you are greeted with panoramic water views from all angles of your exclusive wrap-around balcony. This luxury condo is turnkey furnished with tasteful updates throughout. There are two spacious bedrooms and a third that was converted into a den with a pull-out
Alex Roth ROSEBAY INTERNATIONAL REALTY, INC
$7,500 per month
2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach!Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase.Enjoy a bright, open layout with floor-to-ceiling hurricane
Michele Conn FINE PROPERTIES
$9,000 per month
3605 Fair Oaks Place, Longboat Key, FL 34228
Exceptional Rental Opportunity in Queens HarbourIntroducing a remarkable opportunity to rent a stunning 4-bedroom corner lot residence in the highly sought-after Queens Harbour community, located behind the gates of the Longboat Key Club. This property features a brand new roof and offers the perfect setting for those looking to embrace the Florida lifestyle.The home is filled with abundant
Danielle Gladding COLDWELL BANKER REALTY
$6,500 per month
1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
"SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE OF LONGBOAT KEY. BOOKED FOR FEB-APRIL 2026 and OFF-SEASON MONTHS 2025! Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the unit, you are met with a light, bright and open feeling with the natural
Chrissie Cummings JENNETTE PROPERTIES INC
$9,000 per month
435 L Ambiance Dr Unit H402, Longboat Key, FL 34228
RARELY AVAILABLE! Welcome to L'AMBIANCE! Discover an extraordinary opportunity to rent this luxurious 2-bedroom, 2.5-bathroom condo on the island Longboat Key. Inside the Longboat Key club, this rarely available residence offers 2 car parking spaces (under building garage) private elevator, breathtaking, unobstructed views of the sparkling Gulf of America, complemented by sweeping vistas of lush
Jose Hugo Martinez KW COASTAL LIVING III
$8,000 per month
3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
2-bed, 2-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on
Dakota Magnus FLORIDA GALLERY REAL ESTATE
$13,500 per month
1211 Gulf of Mexico Dr Unit 505, Longboat Key, FL 34228
Welcome to your beachfront retreat on spectacular Longboat Key, Florida. The owners spared no expense to design and equip their home with the best of everything. This is the first time they've ever offered it for lease; it is available as early as August 1, 2025 thru December (3,4 or 5 month occupancy) and also available for the 4 months of January to April. This is 1600 sq ft of beautiful
Sharon Whalen COLDWELL BANKER REALTY
$10,995 per month
2339 Harbour Oaks Dr, Longboat Key, FL 34228
Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has vaulted ceilings with sky lights, and new high impact windows and doors. The open floor plan is perfect for family time and entertaining. The kitchen is very large and has solid cherry wood
Henry Rossi RENT SARASOTA
$14,000 per month
3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
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. Like NEW, this beautifully designed three bedroom luxury residence has just completed a major updating remodeling with all new designer furniture and furnishings, new custom
Patrice Ivan WAGNER REALTY
$3,500 per month
450 Gulf of Mexico Dr Unit B302, Longboat Key, FL 34228
For Rent! Furnished Annual! Step into this beautiful 2 bedroom 2 bathroom condo with pool & water view on Longboat Key. This unit offers the perfect island living from the open floor plan to the scenic view with bay breeze to the supreme location, only 2 miles from St Armand/Lido Key and just 5 miles to Downtown Sarasota. You will never run out of options for both fun and tranquil days! The
Benjamin Dietrich ANCHOR DOWN REAL ESTATE
$18,000 per month
1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero
Melissa Gissinger MICHAEL SAUNDERS & COMPANY
$14,000 per month
531 Birdie Ln, Longboat Key, FL 34228
Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home
Karie Gorgone WAGNER REALTY
$2,800 per month
3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
1-bed, 1-bath paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community's private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community
Dakota Magnus FLORIDA GALLERY REAL ESTATE
$32,000 per month
1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
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
Larry Starr SVN COMMERCIAL ADVISORY GROUP
Showing Results 1 - 40, Page 1 of 4
Sitting 5 miles off the coast from Sarasota, Longboat Key offers luxurious island living without the tourists. “Here we get the island life,” says Maureen Horn, a broker with Michael Saunders & Company, who’s lived on Longboat for 25 years. “This means wearing shorts year-round, being surrounded by water views and going boating whenever you feel like it.”
“Longboat is like an island suburb of Sarasota,” says Horn, “at first people think of it as a vacation spot, then fall in love with it and buy a home.” The Key is about 10 miles long and only ...
Copyright © 2025 CoStar Group
