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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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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White sand beach, blue water, fising, golf, tennis - Longboat KeyAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Smoking OK, Pets OK, TV Description:Spacious airy Villa one block from the beaches referred by many travel magazines as the 'U.S. Caribbean'. Beautiful and tastefully furnished 2 bedroom (king master suite; twins), 2 1/2 baths. Main living area is custom tile with fully equipped kitchen, including everything from small appliances to spoons (totally turnkey). There is also a private attached one car garage with auto door opener. |
House |
2 Beds |
2.5 Baths |
6 People |
$103 - $242 |
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Openings for season February and March - Longboat KeyAmenities:Beach, Ski, Golf Course, Kitchen, Dishwasher, Air Conditioning, Pets OK, TV Description:Vacation Rental Description Adorable and only 50 steps to awesome Longboat beach. This is a very private part of Longboat and often you will not see a soul at any time of year. I was visiting in the height of season and only saw a handful of people.If it is privacy you want you got it. |
Condo |
1 Beds |
1 Baths |
4 People |
$97 - $143 |
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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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Gulf Front - Longboat KeyAmenities:Beach, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Panoramic Gulf and sunset views from all rooms. Nicely turnkey furnished with updated baths. New kitchen appliances. Walk on the beach to dinner at the world renowned Colony restaurant or drive a short distance to St Armand's Circle's shopping and fun. Tennis, recreation room and bike storage, Olympic pool and spa. Secure building in gated community. |
Condo |
2 Beds |
2 Baths |
4 People |
$126 - $126 |
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Sarasota Bay Views-Gulf Beach Access - Longboat KeyAmenities:Beach, Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Panoramic Sarasota Bay Views. Recently remodeled two bedroom, two bath first floor walkout bayfront condo with panoramic views of Sarasota Bay from almost every room. Walk across the street to the beautiful white sand beaches for breathtaking sunsets. Deeded beach access and private beach house. Granite counter tops, tile floors and the latest kitchen appliances, laundry in unit, internet access. |
Condo |
2 Beds |
2 Baths |
6 People |
$65 - $129 |
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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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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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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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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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