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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Beautiful Beach Front Luxury Rental on Longboat KeyAmenities:Beach, Pool, Air Conditioning, TV Description:Spacious, 3 bedroom 2 bathroom condo. This condo located right on the beach on Gulf of Mexico Drive in Longboat Key is tastefully furnished and offers a prime location for beach goers, shoppers, and those who wish to just relax. The condo is minutes away from St. Armands Key an excellent shopping experience, and is located only 10 minutes from downtown Sarasota, which offers fine dining and exciting night life. Including an opera and ballet. The beach is private and quite and the property has i |
Condo |
3 Beds |
2 Baths |
6 People |
$214 - $214 |
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Canal home w/ deeded beach access one block awayAmenities:Beach, Smoking OK, Pets OK Description:Located on Longboat Key, Stargazer is a canal home with beach access one block away. Caged pool and lanai on side of house w/ western exposure. 3bd/2ba fully furnished home. Cable, high speed internet, and phone included. Wooden deck and 10,000 lb. boatlift if you want to rent a boat from a marina. Convenient to everything. |
House |
3 Beds |
2 Baths |
6 People |
$200 - $200 |
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Private Longboat Key Condo with White Sands BeachAmenities:Pool, Air Conditioning, TV Description:Private Island Condo in lush setting. Snuggled between Sarasota Bay and the Gulf of Mexico, a stone throw to either! This unit is hidden and very private. It has a screened in porch overlooking a lush backdrop. The pool is large and great for the kids; the Jacuzzi is nice for the adults and overlooks the pool. The Gulf side has its own private white sands beach perfect for cocktails while watching the sun set. The bay-side has a large grass area perfect for playing, cooking or just looking out |
Condo |
1 Beds |
1 Baths |
2 People |
$196 - $196 |
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Splendid Bay View CondoAmenities:Pool, Air Conditioning, Pets OK, TV Description:Situated close to St. Armand?s Circle and the Van Weizel Performing Arts Center, this Longboat Key vacation rental condo offers breathtaking bay views. Perfect for families and friends, our vacation condo comes replete with enchanting amenities that will make your vacations much more pleasurable. Suitable for up to six guests, our 1 bedroom condo rental Longboat Key comes with a king-size bed, a double bed and a queen-size sofa sleeper. The well fitted full bathroom has been fitted with safety |
House |
1 Beds |
1 Baths |
4 People |
$77 - $77 |
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302 Turtle Crawl 1/1Amenities:Pool, Air Conditioning, TV Description:The owners and I welcome you to this great one bedroom one bath that can sleep up to 6 persons, overlooking the awesome beaches of Longboat Key on the Gulf of Mexico. The view from your 3rd floor private balcony is one of the best in this small Resort complex. This is not a hotel and you find that each condo is different and the owner has gone to extra measures to make her condo a touch of the natural Florida surroundings and the modern comforts of home. Spend your days at the heated pool |
Condo |
1 Beds |
1 Baths |
2 People |
$264 - $264 |
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Splendid Beachfront Condo in Longboat KeyAmenities:Beach, Golf Course, TV Description:Offering spectacular gulf views and sunsets vistas, our Longboat Key, Florida vacation rental is perfect for a classic sun and sand holiday with your family or friends. Beautifully furnished and replete with modern amenities, this splendid retreat is close to numerous recreational and entertainment avenues which include loads of beach fun, water and adventure sports, superb shopping and much more. Featuring designer furnishings, this 1 bedroom condo rental in Longboat Key can easily accommoda |
Condo |
1 Beds |
1 Baths |
2 People |
$269 - $269 |
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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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Home on the Ocean - Long KeyAmenities:Beach, Ski, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Smoking OK, Pets OK, TV Description:This 5 bedroom 5.5 bathroom NEW home on the ocean has tiled floors throughout, 20ft ceilings, fully furnished home equipped with the top of the line Vicking kitchen appliances.The house has a 2 car garage and parking for a further 10 cars,total square footage under air of the home is 3,975 sq ft.Property sits on a private beach with barbacue on the terrace see visual tour for more information. |
House |
5 Beds |
5.5 Baths |
10 People |
$645 - $750 |
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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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