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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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 |
| read more www.alwaysonvacation.com | ||||||
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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 |
| read more www.alwaysonvacation.com | ||||||
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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 |
$145 - $264 |
| read more www.alwaysonvacation.com | ||||||
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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 |
$113 - $196 |
| read more www.alwaysonvacation.com | ||||||
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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 |
$159 - $269 |
| read more www.alwaysonvacation.com | ||||||
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Gulf of Mexico DriveAmenities:Beach, Golf Course, Air Conditioning, Pets OK Description:Contact Owner 8669233905, 9419233905 This Is Living in Paradise! Magnificent breathtaking views of the white sandy beaches & blue waters of the Gulf of Mexico w/panoramic scenery of the pool & Sarasota Bay!This condo has been meticulously maintained in this sought after, centrally located high-rise complex. Located directly on the beach,across from shops, restaurants, public park, golf & tennis! Click Here To See Personal Website |
Condo |
2 Beds |
2 Baths |
4 People |
$183 - $183 |
| read more www.alwaysonvacation.com | ||||||
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Charming Longboat Key RetreatAmenities:Beach, Golf Course, Pool, Air Conditioning, Pets OK, TV Description:Offering the opportunity for a classic sun, sand and surf holiday, our Longboat Key, Florida vacation rental condo is perfect for taking a break from the hustle and bustle of daily routines. If you are looking for a paradise to enjoy incredible ocean and sunset vistas, tropical breezes and a place to relax and recharge, this Longboat Key vacation rental condo will not disappoint you. Comfortably accommodating up to four vacationers, our air-conditioned 2 bedroom rental condo in Longboat Key |
Condo |
2 Beds |
2 Baths |
4 People |
$250 - $350 |
| read more www.alwaysonvacation.com | ||||||
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Beautiful Condo with Stunning Gulf View & Steps from Beach-Avlb'l Nov. & Dec.!Amenities:Pool, Air Conditioning, TV Description:Paradise awaits you in this 2 bedroom, 2 bath condo with a spectacular view of the Gulf of Mexico. Your condo is located in the very well-maintained & centrally located Longboat Terrace Complex which is across the street from the Centre Shops. It is on the 2nd floor of just 2 floors & has a 30 foot screened balcony overlooking the tranquil Gulf of Mexico. You also overlook the large heated pool which is just steps from your door. Enjoy breakfast in the sunny eat-in kitchen or grab a coffee |
Condo |
2 Beds |
2 Baths |
4 People |
$82 - $143 |
| read more www.alwaysonvacation.com | ||||||
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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 - $86 |
| read more www.alwaysonvacation.com | ||||||
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Luxurious Beachfront Retreat in Longboat KeyAmenities:Beach, Pool, Air Conditioning, TV Description:If you are looking towards a luxurious haven for taking a break from the hustle and bustle of your daily routines then our Longboat Key, Florida vacation rental fits the bill perfectly. Part of the Sand Cay Beach Resort which has its own private beach, this charming retreat offers splendid views of the Gulf of Mexico and is close to superb opportunities for water sports and adventures, shopping, fine wining and dining and much more. This centrally air-conditioned 2 bedroom apartment rental in |
Condo |
2 Beds |
2 Baths |
4 People |
$136 - $136 |
| read more www.alwaysonvacation.com | ||||||
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