Encompassing a narrow 12-mile stretch of of sun-kissed beaches and waters, and situated between the Gulf and Sarasota Bay, guests of Longboat Key vacation rentals are treated to superb bayside and oceanfront scenery. Watersport activities are extensive, and guests of Longboat Key rentals will enjoy waterskiing, windsurfing, and sailing. Nearby performing arts centers provide the Longboat Key condo rental guests a sophisticated evening of opera, theater, and ballet. Guests of Longboat Key condos are also treated to a wide selection of nearby golf courses, beautiful waterfront bicycling and scenic boating.
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Longboat Key Vacation Rentals
Longboat Key Vacation Rentals - Search Over 250,000 Listings
| Featured Rentals | Type | Beds | Baths | Sleeps | Rate | |
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ISLAND HOME RETREAT - Little Gasparilla IslandAmenities:Beach, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Breath taking views of beautiful Gasparilla Bay. 1200 square foot living area, newly built home. CLEAN, comfortable and spacious 3 bedroom 2 bath. All the conveniences of home, yet surrounded by the pristine natural elements of a remote island community. Spacious kitchen, dining room, cathedral ceilings, french doors open to a 450 foot screened front porch facing the Bay. |
House |
3 Beds |
2 Baths |
6 People |
$161 - $200 |
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Castle in the Sky near beach and tennis - Longboat KeyAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Pets OK, TV Description:Beautiful 3000 sq ft freestanding condo in beautiful Cedars East tennis resort, situated across the street from the white sands of the Gulf of Mexico. |
Condo |
3 Beds |
2.5 Baths |
9 People |
$97 - $300 |
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Mobile Home - Lower KeysAmenities:Beach, Kitchen, Washer/Dryer, Air Conditioning, TV Description:New Remodel Very Clean Mobile Home. On Clean swiming canal Two queen size beds two bed rooms,living rm kitchen,10 x20 screen porch tv. centeral air. |
House |
2 Beds |
1.5 Baths |
4 People |
$58 - $86 |
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Beautiful Gulf VIew - Longboat KeyAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Description Beautiful Gulf view from this 2 bedroom 2 bath condo newly decorated and furnished. Condo is located on the third floor of the building. Condominum has 45 units and 2 buildings with a total of three floors. Private Beach access directly across the street. (20 minutes from Sarasota Airport; 1 hour from Tampa Airport) |
Condo |
2 Beds |
2 Baths |
4 People |
$87 - $87 |
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POSH like new Bahia Club Isla waterfront&views - Isla Del SolAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:This gorgeous property is like new becuase it virtually is. Upscale everything, largest and newest unit in Isla with exclusive access to Bahia Club with a private pool and spa, exercise room, library and more. |
Condo |
2 Beds |
2 Baths |
6 People |
$66 - $114 |
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Longboat Key Condo Rental - Longboat KeyAmenities:Beach, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Smoking OK, Pets OK, TV Description:Light and bright, this newly renovated condo is only 25 steps to Longboat Key Beach! This area of the beach is very private part and has recently been renourished. If it is privacy you want, this is where to get it! This upstairs unit has all new appliances and includes a dishwasher. You won't be disappointed! |
Condo |
1 Beds |
1 Baths |
2 People |
$93 - $121 |
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New 3/4 Rooftop Spa Home, Steps to Beach! $250/nt! - Lauderdale by the SeaAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Welcome to Villa Vista! This breathtaking 3 Bedroom 4 Bathroom Mediterranean residence is the very definition of a luxury vacation home. Custom built and recently completed in 2008, Villa Vista is situated one block from the beach and downtown area in picturesque Lauderdale By The Sea. This home features a spectacular 1200 square foot rooftop terrace which offers direct city and ocean views! |
House |
3 Beds |
4 Baths |
10 People |
$250 - $250 |
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Best Old Town Location - Key WestAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. |
House |
2 Beds |
2.5 Baths |
6 People |
$70 - $314 |
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Lauderdale By the Sea - Lauderdale Escape 3BR/3BA - Lauderdale by the SeaAmenities:Beach, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:This house is booking fast... This beautiful decorated home is the perfect place to bring the family on vacation. A spacious 'open' floor plan with lots of room to entertain, dine with family or friends, or just enjoy as your personal refuge. Backyard is private and tropical. The furnishings in this home are high quality. There are three bedrooms with 3 baths in a split plan layout with 2 master suites. Everything you could possible want is here. |
House |
3 Beds |
3 Baths |
6 People |
$113 - $250 |
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White sand beach, blue water, fising, golf, tennis - Longboat KeyAmenities:Beach, Ski, Golf Course, Pool, Hot Tub, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Stunning waterfront location in the prestigeous single family neighborhood of Emerald Harbour. Enjoy a lazy 'reading day' at private poolside and hot tub or venture out from your own private dock for boating, fishing, jet ski, kayaking... endless. |
House |
3 Beds |
3 Baths |
6 People |
$103 - $242 |
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