Longboat Key Vacation Rentals

Longboat Key offers vacation rentals on an ideal beach and bayfront setting for the ultimate Florida vacation. Stretching between the gorgeous Gulf of Mexico and serene Sarasota Bay, this key attracts many visitors who come to enjoy the average year-round temperature of 73 degrees. Whether you like to spend your time shelling, biking, shopping, fishing, golfing, playing tennis, or dining, opportunities for these activities are boundless on Longboat Key. We offer some of the best Longboat Key vacation rentals to stay along the beach.

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Showing Results 1 - 15 of 29
Name
Area
Description
448 Gulf of Mexico Dr. A203
Area: Longboat Key
LONGBOAT KEY...enjoy full BAY VIEWS from this split floor plan 2 bedroom, 2 bath condominium located at BAY HARBOUR on the South end of Longboat Key. Both bathrooms have been totally remodeled. New paint, carpet and newly furnished bedroom and living room. The kitchen is equipped with everything you will need for preparing your favorite foods and entertaining. Bay Harbour offers a club room with a pool table, some exercise equipment and a heated Olympic size pool all for your enjoyment. Walk to the Dry Dock or Chart House restaurants. Short drive to Saint Armand's Circle for great shopping and more restaurants. There is plenty to do all within a short distance. Several beach accesses and Mote Marine just over the bridge. Consider this lovely condo for a Seasonal rental (30 days minimum stay) or an Annual rental. LUXURY, GULF OF MEXICO, VACATION RENTAL, SARASOTA BAY.
524 Yawl Lane
Area: Longboat Key
Cute Longboat Key canal home freshly decorated for a seasonal rental. Situated on South Longboat Key with easy access to St. Armand's Circle and downtown Sarasota. Two bedroom, two bathroom single family home that is light and sunny with views of the canal and private pool. The formal dining room is in the front of the house as part of the living room, and the kitchen also has a dinette. Florida room is furnished with couches and a flat screen television. Available summer months, for season or an annual lease, on beautiful Longboat Key in sunny Florida.
250 Sands Point Road #5407
Area: Longboat Key
INN ON THE BEACH ON LONGBOAT KEY LUXURY CONDOMINIUM Deluxe two bedroom and two bath FURNISHED PENTHOUSE. Split floor plan with amazing views from all rooms and large porch deck. Newly furnished and freshly painted ready for your ONE MONTH or longer stay. INN ON THE BEACH ON LONGBOAT KEY is located on the very south end of Longboat Key within the enclave of the Longboat Key Club Resort. Just a a few miles from St Armand's Circle of shops and restaurants and minutes to Downtown SARASOTA. The amenities that are included with your stay are the beachside pool and direct access to the beautiful white sand beach on the Gulf of Mexico. (Note: The restaurants, bars, clubhouse, golf course associated with the Longboat Key Club Resort are not part of the included amenities and are for Members Only).
435 L'Ambiance Drive #807
Area: Longboat Key
Stunning unit behind the gates in sought after Longboat Key. The L'Ambiance is situated on 18 acres on the beautiful sandy beaches of the Gulf of Mexico. The residence is an expansive 2 bedroom, 3 bath unit on the 8th floor with 270 degree views over the Gulf of Mexico, Sarasota Bay, the lush green golf courses of the LBK Club and Sarasota Skyline. Accessed on a private elevator the apartment is 2500 square feet plus a wrap around terrace adding an additional 1000 sq feet. It offers a master bedroom with double bathroom, guest bedroom with full bath, powder room, living room, den dining area and eat in kitchen. Sunrises, sunsets the apartment is bathes in light all day long through floor to ceiling windows in all rooms. The condominium itself sits directly on the beach with a magnificent pool, Jacuzzi, tennis courts, sauna , steam room, gym, running track. pool room, reading room and last, but not least, the Wine Cellar! Perfect for your long term, annual, or seasonal rental!
2045 Gulf of Mexico Dr. #310
Area: Longboat Key
Seaplace is a wonderful, friendly community with lots of activities. This two bedroom, two bath condo is very nicely appointed and is equipped with everything you will need during your stay. There are two pools right on the ocean front, a large, relaxing clubhouse with WIFI. Stroll the beautiful sand on the beach for sunrise and enjoy the evening sunsets. A full open view of the Gulf of Mexico. Great restaurants abound as well as proximity to St Armands Cr for shopping and, numerous craft and art fairs! Short drive to downtown Sarasota and our renowned theatre district. Longboat Key for a delightful vacation. GULF OF MEXICO, LONGBOAT KEY, LUXURY, VACATION RENTAL, SARASOTA.
1935 Gulf of Mexico Drive #211
Area: Longboat Key
SEAPLACE on Longboat Key. Enjoy the wonderful GULF OF MEXICO WATER VIEWS from this THREE bedroom, two bath CORNER UNIT condominium. TURN KEY FURNISHED available. Remodeled bathrooms and kitchen. Two terraces overlooking the Gulf of Mexico. Seaplace amenities include two pools with hot tubs, fitness center, Har-Tru lighted tennis courts, BBQ grills, club house, and fitness center.
 700 Hideaway Bay Lane
Area: Longboat Key
Stunning Longboat Key family retreat. Modern and dramatic four bedroom Luxury custom home to enjoy the grand island style living with all the modern conveniences. Beautiful landscaped corner lot in Longboat Key's Hideaway Bay enclave of homes that includes neighborhood tennis courts and private beach access. Just a short walk to the beautiful Gulf of Mexico and beach. Great open floor plan perfect for entertaining and enjoying the Florida lifestyle. Very private and spacious master suite with views of the pool and canal. Attached poolside cabana style fourth bedroom suite that is pool side with separate entry. Outdoor space is complete with gas grill, swimming pool with solar cover and a boat dock with a lift. Two car garage. Pet Friendly.
1135 Gulf of Mexico Drive #403
Area: Longboat Key
 Enjoy breath taking views of the Gulf of Mexico in this spacious 4th floor 2bdrm./2bath condo on desirable Long Boat Key located in BEACHPLACE I. All rooms have a gulf view with the exception the 2nd bedroom, all tile floors and an open plan with split bedrooms. Amenities include a community pool, clubhouse, fitness center, tennis courts and shuffle board.  No pets allowed.
687 Jungle Queen Way
Area: Longboat Key
Relax in tranquility and style in this fabulous and contemporary architect-designed canal home on Longboat Key. Heated 40' lap pool w/spa, outside decks with view of Sarasota Bay and deeded beach access. Serene, private guest suite with canal view. Great Longboat Key location near beach, St. Armand's Circle and Sarasota. Sub zero freezer, 6 burner Wolf range, many kitchen extras. Bamboo or polished concrete flooring throughout.
616 Buttonwood Drive
Area: Longboat Key
SARASOTA LONGBOAT SHORES**RARE Opportunity: Newly renovated charming home, five minutes walk to the beautiful white sand of the Longboat Key beach on the Gulf of Mexico. Upon your arrival, at the semi-circular driveway, you will be immediately attracted to the mature and stunning tropical vegetation. The winding pave will lead you to the front door. As soon as you step in the house, you will be WOWED by a sense of warm welcome; the spacious living room, dining room, and the simple décor will win your heart. The Florida room has a conversational sofa set, a game table, a bar, and breakfast dining set overlooking the lanai enclosed swimming pool and lush backyard. The kitchen is well equipped with all you need to enhance your enjoyment of living in this tropical paradise. The lovely home also offers two spacious bedrooms, a pullout sleeper, two and half bath, an open office facing the Florida room. This MUST-STAY, clean, and tranquil cottage is waiting for you to experience the coastal living in Tropical paradise. 
1095 Gulf of Mexico Drive #304
Area: Longboat Key
Beautiful 2bdrm. / 2bath condo overlooking a tranquil reflection pond with views of the beach from the balcony. Recently remodeled with granite countertops and birch cabinets in kitchen and bathrooms, tile floors throughout and stainless steel appliances. King size bed in master bedroom and twin beds in the spare bedroom. Upgraded electronics include high speed internet and 48” flat screen TV with HD / DVR cable box. Located in meticulously landscaped Beachplace complex with an Olympic size heated pool including 2 lap lanes, a huge whirlpool spa, 3 tennis courts and a clubhouse with a fitness center – all within steps of miles and miles of sand beaches.
1906 Harbourside Drive #301
Area: Longboat Key
End unit townhouse in Fairway Bay, with a boat dock.  All new decorating in this light and spacious unit that has a view of the canal.  Lots of windows and two stories with skylights giving the unit loads of light.  Living room is two stories with a vaulted ceiling.  All new decorating, two master suites with King and Queen sized beds, two dens with double fold out couches.  One of the master suites is on the main living area.  Private two car garage. 
1975 Gulf of Mexico Drive, #208
Area: Longboat Key
SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the master suite. Master bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST ARMANDS CIRCLE of restaurants, shops and entertainment..
1095 Gulf of Mexico Drive, #101
Area: Longboat Key
Wonderful first floor walk out.  Direct Gulf views, pool and lake views.   This unit has been completely redone top to bottom.  Professionally decorated with 17 inch tile throughout, granite in the kitchen and bathrooms, maple cabinets throughout. Longboat Key/Vacation/Rental/Holiday
1925 Gulf of Mexico Drive #208
Area: Longboat Key
Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Master Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive white sand beach on the Gulf of Mexico.

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