$15,000 Per Month
1211 Gulf of Mexico Dr, Longboat Key, FL 34228
Gorgeous gulf front vacation rental available now through 2027!! You will love this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the
$13,500 Per Month
1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
**Prime Location – Luxurious Waterfront Living at Promenade, Longboat Key**This absolutely gorgeous condo is located in the prestigious Promenade on Longboat Key, offering breathtaking water views from every room. The residence features 2 bedrooms plus a den and 2 bathrooms. The spacious master suite includes a king-size bed and an elegant en-suite bathroom with a separate bathtub, walk-in
Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE
$11,000 Per Month
775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
AVAILABLE DEC. '26 THROUGH FEB.'27. Beautiful 9th floor, 1600 sq. ft. 2 bedroom 2 bath at the sort after Beaches condominium which is within the gates of the Longboat Key Club. Updated kitchen and bathrooms. Fabulous bay, and Longboat Key Club golf views. Wrap around balcony with partial Gulf view. Washer/dryer in the unit, pool, fitness center and tennis courts plus 24 hr. Concierge and garage
Brenda Cozy COLDWELL BANKER REALTY
$6,684
Total Monthly Price
4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
The advertised rate of $6,684/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 10, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$7,700
Total Monthly Price
5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
The advertised rate of $7,701/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 18, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$3,500 Per Month
1930 Harbourside Dr Unit 122, Longboat Key, FL 34228
Wonderful 2 bedroom 2 bath condo in Fairway Bay community on Longboat Key. Condo is being rented fully furnished and is available at a 2 month minimum rental. this is totally updated and ready to move in. amazing Bay views to enjoy and community has lots of amenities from Tennis, pool, spa, beach access and 24/7 security. All renters need to be approved by association, and application fee is
David Leventhal COLDWELL BANKER REALTY
$2,800 Per Month
730 Spanish Dr S Unit 99, Longboat Key, FL 34228
Experience the pinnacle of coastal living in this beautifully updated, ground-floor condominium in the highly desirable Spanish Main Yacht Club on Longboat Key. This 2-bed, 2-bath residence offers 1,255 sq. ft. of bright, air-conditioned space featuring elegant engineered hardwood floors, modern stone kitchen countertops, and a welcoming living/dining room combination ideal for entertaining. The
Geoff Scalera AUM FLORIDA REAL ESTATE LLC
$9,500 Per Month
1975 Gulf of Mexico Dr Unit G4401, Longboat Key, FL 34228
Perched on the top floor with nothing between you & the water, this fully furnished beachfront retreat at Seaplace offers unobstructed Gulf of America views from every room. Living, dining & kitchen face the Gulf; the king primary suite opens to a private beachfront balcony, the second bedroom (two twins) has its own, and a flexible 3rd room with a Murphy bed works as a bedroom, media room, or
Robert Hildreth THE AGENCY SARASOTA
$78,000 Per Month
1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
An exceptionally rare opportunity to lease one of the most exclusive waterfront residences ever offered on Florida’s Gulf Coast. Positioned within the iconic St. Regis Residences on Longboat Key, this extraordinary four-bedroom, four-and-a-half-bath condominium redefines annual luxury living with an unrivaled level of privacy, sophistication, and world-class service. Arrive via private elevator
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$3,000 Per Month
820 Spanish Dr S, Longboat Key, FL 34228
Coastal Living at Its Finest in the Spanish Main Yacht Club! Discover your perfect Florida retreat in this beautifully maintained, free-standing 2-bedroom, 2-bathroom villa located on the highly coveted southern end of Longboat Key at 820 Spanish Dr S. Offering 1,390 square feet of bright, open living space, this single-story residence perfectly blends maintenance-free comfort with an active,
Geoff Scalera AUM FLORIDA REAL ESTATE LLC
$2,400 Per Month
450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
Annual furnished rental: Discover the ultimate island lifestyle in this comfortably furnished 2-bedroom, 2 bath, unit located in the highly sought-after community of Bay Harbour on the southern end of Longboat Key. Just minutes from St. Armands Circle, downtown Sarasota, restaurants, shopping, county tennis and pickleball courts, walking trails, parks and of course – Longboat Key public beach
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
$4,995 Per Month
2020 Harbourside Dr Unit 446, Longboat Key, FL 34228
Experience luxury island living in this beautifully remodeled 2-bedroom, 2-bath residence located in the highly sought-after Fairway Bay community within Bay Isles on Longboat Key. Available for immediate occupancy, this turnkey furnished coastal retreat offers flexible lease terms from 6 to 12 months.Step inside to discover a bright and open floor plan featuring upscale contemporary
Jeffrey Swanson VIVE REALTY
$4,000 Per Month
1000 Longboat Club Rd, Longboat Key, FL 34228
Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for
$2,950 Per Month
909 Spanish Dr N Unit 51, Longboat Key, FL 34228
Virtually Staged. 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
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY
$4,200 Per Month
840 Bayport Way Unit 840, Longboat Key, FL 34228
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
Shirley Cuddy REALTY SERVICES INC
$6,000 Per Month
1050 Longboat Club Rd Unit 803, Longboat Key, FL 34228
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
Melissa Kontny XCELLENCE
$5,000 Per Month
3210 Bayou Sound, Longboat Key, FL 34228
4TH OF JULY SPECIAL - 1ST MONTH ONLY $5,000. 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
Richard Ivan WAGNER REALTY
$5,950 Per Month
2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
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
Richard Ivan WAGNER REALTY
$7,850 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. 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
Patrice Ivan WAGNER REALTY
$2,500 Per Month
3802 Gulf of Mexico Dr, Longboat Key, FL 34228
AVAILABLE FOR ANNUAL OR 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
$15,000 Per Month
1591 Gulf of Mexico Dr, Longboat Key, FL 34228
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
$4,500 Per Month
601 Longboat Club Rd Unit 1004S, Longboat Key, FL 34228
Property Id: 2517125This beachfront retreat offers breathtaking panoramic views from its Gulf-front and east-facing balconies, encompassing Lido and Siesta Keys, Longboat Key, and the Sarasota skyline. Inside, a sunlit living room with large windows, a dining area with ocean views, and an updated kitchen with stainless steel appliances and an in-unit washer/dryer provide comfortable
$5,500 Per Month
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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
Scott Nold TNG PROPERTY MANAGEMENT
$6,950 Per Month
2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
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
Andrew Clark SECURE DOOR PROPERTY MANAGEMENT
$16,000 Per Month
2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
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
Michele Conn PREFERRED SHORE LLC
$6,500 Per Month
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
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.
John Schafer, V COLDWELL BANKER REALTY
$2,500 Per Month
3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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
Brigette Marcus NEXTHOME EXCELLENCE
$4,000 Per Month
1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for
Cody Smith RENT SARASOTA
$8,000 Per Month
3040 Grand Bay Blvd, Longboat Key, FL 34228
Experience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and sophistication, this residence offers the elegance of a luxury waterfront home with the
$3,500 Per Month
4330 Falmouth Dr, Longboat Key, FL 34228
Longboat Key Beach and Bay Access.2 Bedroom 2 Bathroom First Floor condo in a gated community with tons of amenities.✅ Deepwater channel with docks and slips available up to 34' (on waitlist)✅ Amazing water views & breezes✅ Private deeded beach access (private building on beach with showers + bathrooms, benches and tables!)✅ 4 Pools, clubhouse, gym, sauna,
$12,000 Per Month
2425 Gulf of Mexico Dr, Longboat Key, FL 34228
Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath
$7,000 Per Month
537 Outrigger Ln, Longboat Key, FL 34228
Welcome boating enthusiasts to this exceptional waterfront residence located in the highly desirable Country Club Shores community on Longboat Key. Situated on a deep-water canal with direct access to the Gulf of America, this beautifully updated two-bedroom, two-bath home with a den offers the ultimate island lifestyle for boaters and beach lovers alike. The property features a brand-new
$6,500 Per Month
3240 Gulf of Mexico Dr, Longboat Key, FL 34228
Seasonal / Short-Term Rental on Longboat KeyVacation in one of the nation’s most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated and
$19,975 Per Month
5801 Gulf of Mexico Dr, Longboat Key, FL 34228
Welcome to your own Gulf-front retreat on Longboat Key!This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views.Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows that bring in natural light and frame the Gulf.The
$5,950 Per Month
2013 Harbour Links Dr, Longboat Key, FL 34228
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
$15,000 Per Month
1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
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
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$9,900 Per Month
4805 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
Property Id: 2484818Available December 1st, 2026, January 2027, and February 2027! (December has a discount!) THE OCEAN IS YOUR BACKYARD! Minutes away from world-class golfing, boating, tennis, dining, and shopping. This exclusive, private, and serene Gulf Coast Condominium unit has been a traveler's dream for so many years now. The Property offers steps to the Gulf Coast's richest
$4,200 Per Month
3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
Looking next season (2026-2027) Lease or Lease/Option - Owner looking to lease up to 6 Months $4200 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
Len Scavron LEN SCAVRON
$4,500 Per Month
6980 Poinsetta Ave, Longboat Key, FL 34228
Tucked away in a quiet fisherman’s village on Longboat Key, this elegant one-bedroom cottage blends classic island charm with modern luxury.The bright, open living space features soaring vaulted ceilings and a sleek, contemporary kitchen. Premium comforts include high-speed internet, in-unit laundry, a reverse osmosis water filtration system, and UV air purification.Perfect for couples
Christina Vescovo LPT REALTY, LLC
$5,500 Per Month
5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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
Matt Darak DARAK GROUP INCORPORATED
Showing Results 1 - 40, Page 1 of 4
There are currently 152 homes available for rent in Longboat Key, FL. The median rent is $7,158 per month, with single-family homes renting at $10,500, townhouses at $13,000 and condos at $6,975.
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Number of Homes for Rent
152
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Median Rent
$7,158
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Median Single Family Home Rent
$10,500
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Median Townhouse Rent
$13,000
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Median Condo Rent
$6,975
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