$13,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
806 Bayport Way Unit 806, Longboat Key, FL 34228
806 Bayport Way Unit 806, Longboat Key, FL 34228
97
Homes for Rent in Longboat Key, FL with 2-Bedrooms
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$3,243
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,388 Sq Ft
- Condo for Rent
1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228The advertised rate of $3,243/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 19, 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
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$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
817 Bayport Way Unit 817, Longboat Key, FL 34228
817 Bayport Way Unit 817, Longboat Key, FL 34228 -
$11,000 Per Month
- 2 Beds
- 2 Baths
- 1,370 Sq Ft
- Condo for Rent
807 Bayport Way, Longboat Key, FL 34228
807 Bayport Way, Longboat Key, FL 34228Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM
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$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,426 Sq Ft
- Condo for Rent
741 Bayport Way Unit 741, Longboat Key, FL 34228
741 Bayport Way Unit 741, Longboat Key, FL 34228 -
$19,798
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,065 Sq Ft
- Condo for Rent
4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228The advertised rate of $19,799/month is the lowest available price, based on a 1 month(s) and 1 day(s) stay with a move-in date of February 18, 2028.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
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$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
833 Bayport Way Unit 833, Longboat Key, FL 34228
833 Bayport Way Unit 833, Longboat Key, FL 34228 -
$5,508
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,388 Sq Ft
- Condo for Rent
1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228The advertised rate of $5,508/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 22, 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
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$9,000 Per Month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
829 Bayport Way Unit 829 B, Longboat Key, FL 34228
829 Bayport Way Unit 829 B, Longboat Key, FL 34228 -
$7,524
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,184 Sq Ft
- Condo for Rent
5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228The advertised rate of $7,524/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 26, 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
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$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,346 Sq Ft
- Condo for Rent
5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228 -
$4,354
Total Monthly Price
- 2 Beds
- 1.5 Baths
- 871 Sq Ft
- Condo for Rent
779 St Judes Dr N Unit SI FL2-ID1604522P, Longboat Key, FL 34228
779 St Judes Dr N Unit SI FL2-ID1604522P, Longboat Key, FL 34228The advertised rate of $4,355/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 5, 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
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$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
522 Bayport Way Unit 522, Longboat Key, FL 34228
522 Bayport Way Unit 522, Longboat Key, FL 34228 -
$10,500 Per Month
- 2 Beds
- 2 Baths
- 1,513 Sq Ft
- Condo for Rent
2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228
2425 Gulf of Mexico Dr Unit 7F, Longboat Key, FL 34228 -
$11,000 Per Month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
739 Bayport Way Unit 739, Longboat Key, FL 34228
739 Bayport Way Unit 739, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
830 Bayport Way Unit 830, Longboat Key, FL 34228
830 Bayport Way Unit 830, Longboat Key, FL 34228 -
$13,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
609 Bayport Way Unit 609, Longboat Key, FL 34228
609 Bayport Way Unit 609, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
805 Bayport Way Unit 805, Longboat Key, FL 34228
805 Bayport Way Unit 805, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
720 Bayport Way Unit 720, Longboat Key, FL 34228
720 Bayport Way Unit 720, Longboat Key, FL 34228 -
$10,000 Per Month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
519 Bayport Way Unit 519, Longboat Key, FL 34228
519 Bayport Way Unit 519, Longboat Key, FL 34228 -
$6,000 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
517 Bayport Way Unit 517, Longboat Key, FL 34228
517 Bayport Way Unit 517, Longboat Key, FL 34228 -
$10,500 Per Month
- 2 Beds
- 2 Baths
- 1,514 Sq Ft
- Condo for Rent
615 Dream Island Place Unit 201, Longboat Key, FL 34228
615 Dream Island Place Unit 201, Longboat Key, FL 34228 -
$11,500 Per Month
- 2 Beds
- 2 Baths
- 1,531 Sq Ft
- Condo for Rent
724 Bayport Way Unit 724, Longboat Key, FL 34228
724 Bayport Way Unit 724, Longboat Key, FL 34228 -
$4,500 Per Month
- 2 Beds
- 2 Baths
- 1,449 Sq Ft
- Condo for Rent
6700 Gulf of Mexico Dr Unit 117, Longboat Key, FL 34228
6700 Gulf of Mexico Dr Unit 117, Longboat Key, FL 34228RARE UNFURNISHED ANNUAL Longboat Key Whitney Beach 2-bedroom, 2 full bath 1st floor end-unit located on the serene north end of Longboat Key. This waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou from Livingroom, master bedroom, dining area and kitchen. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout,
Kim Blakeney JENNETTE PROPERTIES INC
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$12,000 Per Month
- 2 Beds
- 2 Baths
- 1,470 Sq Ft
- Condo for Rent
2425 Gulf of Mexico Dr, Longboat Key, FL 34228
2425 Gulf of Mexico Dr, Longboat Key, FL 34228Escape 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
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$3,600 Per Month
- 2 Beds
- 2 Baths
- 1,015 Sq Ft
- House for Rent
420 Firehouse Ct Unit 10, Longboat Key, FL 34228
420 Firehouse Ct Unit 10, Longboat Key, FL 34228Seldom available annual rental on the coveted north end of Longboat Key. This beautifully remodeled 2-bedroom, 2-bath condo boasts new appliances, cabinets, flooring, and modern fixtures throughout. Both bedrooms feature spacious walk-in closets, and a separate utility room includes washer and dryer hookups. Embrace the laid-back coastal lifestyle with quick access to beaches, restaurants,
Gregory Koss WAGNER REALTY
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$11,000 Per Month
- 2 Beds
- 2 Baths
- 1,370 Sq Ft
- Condo for Rent
807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM
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$2,600 Per Month
- 2 Beds
- 2 Baths
- 1,423 Sq Ft
- Condo for Rent
885 Spanish Dr N, Longboat Key, FL 34228
885 Spanish Dr N, Longboat Key, FL 34228This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features tile flooring throughout, a spacious chef’s kitchen, granite island and counters, and new appliances—all opening to a bright living area. The primary suite offers an en-suite bath with new tile shower and granite counter plus a
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$4,800 Per Month
- 2 Beds
- 2.5 Baths
- 1,755 Sq Ft
- House for Rent
616 Lyons Ln, Longboat Key, FL 34228
616 Lyons Ln, Longboat Key, FL 34228Come and enjoy a little piece of Paradise! This beautiful canal front home is located in the idyllic and picturesque Longboat Key. A charming mid-century style cottage nestled in one of Longboat Key's most private and serene settings. This spacious 2 bedroom + Bonus room, 2.5 bathrooms with outdoor shower residence offers 1,755 square feet of luxurious living space perfect for those seeking a
Steve Barthelemy ROOST REALTY INC.
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$3,000 Per Month
- 2 Beds
- 2 Baths
- 1,390 Sq Ft
- Condo for Rent
820 Spanish Dr S, Longboat Key, FL 34228
820 Spanish Dr S, Longboat Key, FL 34228Coastal 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
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$4,000 Per Month
- 2 Beds
- 2 Baths
- 1,423 Sq Ft
- Condo for Rent
706 Spanish Dr S, Longboat Key, FL 34228
706 Spanish Dr S, Longboat Key, FL 34228Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after, active 55+ community of Spanish Main Yacht Club! Ideally situated just steps from the marina, this 2-bedroom, 2-bathroom villa features a bright Florida room and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. It is
Geoff Scalera AUM FLORIDA REAL ESTATE LLC
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$7,000 Per Month
- 2 Beds
- 2 Baths
- 1,133 Sq Ft
- Condo for Rent
3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You
Andy Moore GULF COAST REALTY & MANAGEMENT
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$5,500 Per Month
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
- Condo for Rent
4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk
Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$3,500 Per Month
- 2 Beds
- 2.5 Baths
- 1,590 Sq Ft
- Condo for Rent
2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural
Alex Larchenko KELLER WILLIAMS ON THE WATER S
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$4,000 Per Month
- 2 Beds
- 2 Baths
- 1,106 Sq Ft
- Condo for Rent
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228Tucked 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.
Janette Schafer COLDWELL BANKER REALTY
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$6,900 Per Month
- 2 Beds
- 2.5 Baths
- 1,440 Sq Ft
- House for Rent
535 Forest Way, Longboat Key, FL 34228
535 Forest Way, Longboat Key, FL 34228Welcome 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
Andy Moore GULF COAST REALTY & MANAGEMENT
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$4,200 Per Month
- 2 Beds
- 2 Baths
- 1,640 Sq Ft
- Condo for Rent
840 Bayport Way Unit 840, Longboat Key, FL 34228
840 Bayport Way Unit 840, Longboat Key, FL 34228This 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
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$5,500 Per Month
- 2 Beds
- 2 Baths
- 1,561 Sq Ft
- Condo for Rent
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228A 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
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$11,000 Per Month
- 2 Beds
- 2 Baths
- 1,642 Sq Ft
- Condo for Rent
1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228Rented 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
Margaret Young JENNETTE PROPERTIES, INC.
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$5,700 Per Month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228VACATION RENTAL!!! AVAILABLE JAN - MARCH 2027! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your
Diann Thelen GULF COAST RENTAL HOMES&CONDOS
Showing Results 1 - 40, Page 1 of 3
2-Bedroom Rental Home Trends in Longboat Key, FL
There are currently 97 homes available for rent in Longboat Key, FL. The median rent is $7,000 per month, with single-family homes renting at $11,000, townhouses at $13,000 and condos at $6,500.
Rental Home Trends
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Number of 2 Bedroom Homes for Rent
97
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Median 2 Bedroom Condo Rent
$6,000
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Median 2 Bedroom Townhouse Rent
$13,000
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Rentals in Longboat Key
Homes for Rent by Bedrooms in Longboat Key
Rentals by Price in Longboat Key
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