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 30
Name
Area
Description
530 Putting Green Lane
Area: Longboat Key
Wonderful Country Club Shores home on a canal with a screened pool. Enter through the front door to a lovely light living room with a view of the pool and canal. Formal dining room and eating space in the large kitchen as well. The master bedroom features a king sized bed and bathroom with a shower, the second bedroom also has a king sized bed, and the third bedroom has a queen sized bed. This is a spacious three bedroom home with a two car garage, and just minutes from St. Armands Circle. LONGBOAT KEY CANAL HOME
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.
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..
3630 Gulf of Mexico Drive #301
Area: Longboat Key

LONGBOAT KEY..This three bedroom, 2 bath corner unit has both full GULF VIEWS from one screened balcony for watching gorgeous sunsets after a day at the beach and, full BAY VIEWS from the second screened balcony. Kitchen and bathrooms have been newly renovated with granite counters. Beautiful new tile flooring installed on the diagonal makes this unit feel even larger than it is and new carpet in the bedrooms. Full sized laundry room in the unit. Just a few steps across the street is a PRIVATE BEACH for Buttonwood residents. The private boat slip on SARASOTA BAY assigned to this unit will accommodate a 30' boat. Enjoy the amenities available for your use, TENNIS COURTS, RACQUET BALL COURTS, club house overlooking the BAYFRONT HEATED POOL. Glass doors enclosing the balcony allows this large room to be used as a FLORIDA ROOM in all weather. Extra storage for bikes. Mid-key location is very convenient to shopping, restaurants etc. This unit is also being offered as an annual.

1975 Gulf of Mexico Drive #302
Area: Longboat Key
Meticulously maintained loft condo in desirable G4 beachfront building. Accommodates up to 4 guests. This is the owners second home and is not a typical rental. An open and airy gr3eat room with vaulted ceilings. Completely remodeled and tastefully decorated with Ethan Allen furnishings and original artwork. Granite and Stainless in the fully equipped gourmet kitchen. The master bedroom is spacious with generous closet space. En-suite Washer/Dryer, Blue Ray, Two TVs, DVD WIFI access, HP Printer, large lanai with garden and tennis court views. If you are looking for a beautiful immaculate rental this is a must see. 
2295 Gulf of Mexico #115
Area: Longboat Key
LONGBOAT KEY...ISLANDER CLUB. Two bedroom, two bath condo directly on the beach with a view of the Bay, Bay Isles wooded area and the Golf course. Open floor plan, living room dining room combo. There are sliding glass doors in all the rooms that lead to the covered patio area. Plenty of closets and storage space. On site management staff. Amenities include an Olympic size pool on the beach. Fitness center and elegant community room both facing the ocean. Two lighted tennis courts, billiard room, sauna, library and two fishing piers. Close to shopping, restaurants, St Armands Circle and downtown Sarasota. LONGBOAT KEY, SARASOTA, VACATION RENTAL, LUXURY.
3221 Bayou Way
Area: Longboat Key
Everywhere you look from top to bottom, this private garden home in the Bayou Section of Bay Isles has been upgraded. Landscaping that is manicured and mature gives you privacy, but also functionality. Double door entry leads into the beautiful hardwood flooring in the separate living room and dinning room to the high ceiling expansive great room which opens into the kitchen and a separate breakfast area with windows all around. The French doors lead to the lanai overlooking the brick paver pool area, all screened enclosed. No stone unturned in this impeccably maintained residence. Plenty of space below with rec room, pool table, work bench and closeted storage. Master bedroom with entry to the lanai, guest bedroom with en suite and a third bedroom includes a total of three bedrooms, three and one half baths. Enjoy the Bay Isles Beach Club on the Gulf of Mexico is included. You may join the Longboat Key Club for access to their amenities including the marina, restaurants, tennis and golf .
 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.
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.
2045 Gulf of Mexico Drive #305
Area: Longboat Key
Gorgeous, spacious, end unit with fantastic views of the Gulf of Mexico. This beautiful condo has been renovated throughout with new bathrooms, Italian porcelain flooring throughout. It is booked for Jan-March 2017. Available now through the summer and fall.
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. 
1105 Gulf of Mexico Drive #101
Area: Longboat Key
Sarasota Gulf front condo for lease! Light and bright residence with spacious entry. Enjoy the lovely view of the pond with its enchanting fountain along with partial Gulf of Mexico views from this first floor walk-down that is perfect for families. The large, open kitchen is well maintained and is complimented with a breakfast bar and the master bedroom has it's own private access to the spacious terrace. Large, neutral colored tile throughout the main area and nicely carpeted bedrooms are perfect for families that like to spend the day at the beach. Beachplace amenities include a heated pool, spa, fitness center, tennis courts, on site management, bike room, chair room.
560 Golf Links Lane
Area: Longboat Key
ATTENTION BOATERS-COUNTRY CLUB SHORES of LONGBOAT KEY. 4 bedroom, 4 bath updated 2 story pool home is ready for you. A 65' boat dock with a 16,000 lb. electric boat lift on a deep canal with no bridges for easy access to the Bay. Screened in heated pool with a built in outdoor grill perfect for entertaining. Open floor plan with a wet bar in the kitchen with a pass through window to the lanai. Fourth bedroom on the second floor is a full suite with it's own bathroom. Great furnishings throughout this lovely home. Available for Season, off season or an Annual rental. GULF OF MEXICO, LONGBOAT KEY, VACATION RENTAL, SARASOTA.
4 Winslow Place
Area: Longboat Key
LONGBOAT KEY..This lovely 3 bedroom, 2 bath home is ideally located on CRANE'S BAYOU, which is just a stone's throw away from SARASOTA'S OPEN BAY. This charming home in Buttonwood Harbor offers tray ceilings, tile and wood flooring throughout, an open kitchen, waterfront pool deck, plus a dock and lift on sailboat water. The dining/living room features a wall of French doors that extend the space to the outdoor entertaining area and showcase wonderful views. The updated kitchen, which overlooks the family room, includes stainless steel appliances, corian countertops, tile backsplash and solid wood cabinets. Enjoy the master suite with direct access to the pool deck while your guests relish in their own privacy. BUTTONWOOD HARBOUR IS A QUAINT, SECLUDED community located on the BAY FRONT OF LONGBOAT KEY, comprised of custom-designed homes and is centrally located near Publix Market, Longboat Key Club's Harbourside facility, St. Armand's Circle and downtown Sarasota, Beach access is only a short walk away.
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.

Showing Results 1 - 15 of 30
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