Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has
Amazing 4 bedroom + den/office, 5.5 bathroom house in Longboat Key. Amenities included: balcony, central air, central heat, deck, dishwasher, pool, updated kitchen, updated bathroom, storage, washer d
This EXQUISITE 3 bedroom - 3 1/2 bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open floor plan with plenty of space for living, dining and entertaining and custom a
RARELY AVAILABLE FURNISHED GULF FRONT ANNUAL RENTAL! At Water's Edge is a stunning beachfront property that offers a luxurious and memorable experience. Its modern and dramatic exterior provides a hin
*Rented for Season 2025* 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 walkin
Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathr
Welcome to Sea Duced! Rarely available beachfront 3 bedroom, 3 bath townhouse with a private indoor pool located on the stunning, Longboat Key. Designed by Sarasota School of Architecture co-founder T
Directly on the GULF. PRIVATE BEACH Be Prepared for style, relaxation and Longboat luxury in this completely renovated condo. Unit was renovated in 2023. Call for rates and availability.
LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds a
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$15,000/mo
3 beds3 baths1,710 sq ft
1465 Gulf of Mexico Dr #504, Longboat Key, FL 34228
Rent is $15,000 monthly off season and $25,000 monthly for the season beginning in December to the end of April. Possibility renting for one year. Best rental in Longboat Key, lushly landscaped locati
Rented for All of Season 2025. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floorplan, the kitchen and family room are
GORGEOUS INSIDE! This beautifully remodeled ground floor, corner unit, features 3 bedrooms, 2 bathrooms with an open concept floor plan. This home welcomes you into an expansive Living/Dining/Kitch
LUXURY LIVING...behind the gates of LONGBOAT KEY CLUB. Spacious two bedroom, 3 bath condo with a FABULOUS VIEW OF THE GULF OF MEXICO and the SARASOTA BAY FRONT. A huge wrap around balcony to enjoy you
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$13,000/mo
2 beds2.5 baths2,385 sq ft
435 L Ambiance Dr Unit H402, Longboat Key, FL 34228
Unique 3 bedrooms and 3 bathrooms property in Longboat Key, Bay Isles community has a lot to offer to prospective long term renters. Set in The Bayou behind 2 security gates. House was remodeled in th
Available to book 2025 season, 4 month minimum! Sea Gate Club! Direct Gulf Views! This stunning 2nd floor residence features 2 bedrooms and 2 full baths with floor to ceiling windows in every room fo
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$12,500/mo
2 beds2 baths1,513 sq ft
2425 Gulf of Mexico Dr Unit 2A, Longboat Key, FL 34228
SEASONAL: AVAILABLE FOR 2025 SEASON! 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
Welcome to Beachfront Paradise! This stunning waterfront second-floor, 2-bedroom, 2.5 bath two-story condo is located in the exclusive community of Seaplace in Longboat Key. The location is everything
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$12,369/mo
2 beds2.5 baths1,214 sq ft
2089 Gulf of Mexico Dr Unit G1-204, Longboat Key, FL 34228
Boater's Dream! Annual Lease. Turnkey & Fully Furnished - Dive into the heart of paradise with this enchanting mid-century canal-front home, currently available for an annual rental, completely turnke
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 p
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$12,000/mo
2 beds2 baths1,411 sq ft
4325 Gulf of Mexico Dr #408, Longboat Key, FL 34228
Gorgeous Gulf front, turnkey furnished rental in Tiffany Plaza. Walk out to the beach from this lovely updated and exquisitely furnished 2 bed/2 bath condo. Coastal inspired decor, king bed in the pri
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$12,000/mo
2 beds2 baths1,336 sq ft
4325 Gulf of Mexico Dr #102, 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 t
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$12,000/mo
2 beds2 baths1,470 sq ft
2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
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 bathroo
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$12,000/mo
3 beds2 baths1,839 sq ft
1485 Gulf of Mexico Dr #109, Longboat Key, FL 34228
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 tru
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$12,000/mo
2 beds2 baths1,598 sq ft
1211 Gulf of Mexico Dr #405, Longboat Key, FL 34228
Open for season 2025. Looking for 3 month renter January through March 2025. Direct Beachfront, Longboat Key remodeled 2/2 Condo in Beachplace. Beautiful Beachplace is a gated community located on th
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$11,700/mo
2 beds2 baths1,392 sq ft
1045 Gulf of Mexico Dr #402, Longboat Key, FL 34228
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 car
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$11,400/mo
2 beds2 baths1,503 sq ft
1135 Gulf of Mexico Dr #504, Longboat Key, FL 34228
Available January 2025. Leased February - April 2025. Available May 8, 2024 - January 31, 2025. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHP
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$11,000/mo
2 beds2 baths1,642 sq ft
1125 Gulf of Mexico Dr #403, Longboat Key, FL 34228
LEASED 2025 SEASON! RARE FIND on south LONGBOAT KEY. Absolutely gorgeous tranquil Gulf of Mexico views from most rooms in this lovely 1900 sq. ft. 3 bedroom 2 bath plus den. 3rd floor condo in eleva
Available July through December 2024. July, August, September, October are available for $10,000 per month. November and December are available for $15,000 per month. Welcome to paradise on Longboat K
***NEW VACATION RENTAL LISTING** Rented for Season 2025 February through April 15th.* Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex lo
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$10,000/mo
2 beds2 baths1,463 sq ft
2109 Gulf of Mexico Dr #1203, Longboat Key, FL 34228
Monthly/Seasonal Availability & Pricing:Our Longboat Key Beachside Bliss condo, located at Beachplace on Longboat Key is available for monthly/seasonal rental.Minimum 30-day stays, open to stays up to
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$10,000/mo
2 beds2 baths1,503 sq ft
1095 Gulf of Mexico Dr #504, Longboat Key, FL 34228
" short stories'...Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the i
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$9,871/mo
3 beds2.5 baths1,336 sq ft
4325 Gulf of Mexico Dr #507, Longboat Key, FL 34228
Welcome to Haven on Hughes! This one-of-a-kind 4-bedroom, 2-bath, two-story spacious pool home is located on the Historic North End of gorgeous Longboat Key. The location of Haven on Hughes is perfect
short stories FEBRUARY, MARCH AND APRIL 2024 ARE AVAILABLE. Stunning 2 bedroom 2 bath Longboat Key gulf front condo with direct sweeping views of the Gulf of Mexico. Every evening enjoy breathtakin
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$9,721/mo
2 beds2 baths1,837 sq ft
2105 Gulf of Mexico Dr #3401, Longboat Key, FL 34228
Last Minute Availablity: December 1, 2023 - January 31, 2024 Booked: February - May 6, 2024 Stay right on the edge of the Gulf of Mexico and enjoy Direct Gulf views from multiple vantage points within
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$9,500/mo
2 beds2 baths1,409 sq ft
1050 Longboat Club Rd #906, 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 y
Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes fullyfurnished and equipped with flat screen TV's, cable and WiFi.
Seasonal rental in Bayport Beach and Tennis Club which is a beautiful, established, award-winning, amenity-rich community with immediate access to a peaceful private beach that continues in both direc
Available 2025 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the
LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic sce
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$9,000/mo
3 beds3 baths2,698 sq ft
1925 Gulf of Mexico Dr #309, Longboat Key, FL 34228
Based on information submitted to the MLS GRID as of Tue May 07 2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.