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.

TOUR THE SEAPLACE COMMUNITY


Showing Results 1 - 15 of 31
Name
Area
Description
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.
1945 Gulf of Mexico Drive #303
Area: Longboat Key
Tastefully furnished condo with updated kitchen & baths. Appointments include stone flooring, granite counters, cherry cabinets and new lighting throughout. Conveniently located next to the main club house and pool. Seconds to the white sandy beach. Two plasma TV's. Two parking spaces. Great seasonal opportunity.
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 .
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.
1975 Gulf of Mexico Drive, #208
Area: Longboat Key
Relax in this beautifully remodeled 2 bedroom 2 bathroom condo in Seaplace. You will love what has been done. Sleeping accomodations include a comfortable king in the master and a single day bed in the 2nd. There is also a Jacuzzi tub in the 2nd bath with G-4 overlooking the tennis courts. LONGBOAT KEY/VACATION/HOLIDAY/RENTAL.
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. 
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
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.
597 Yawl Lane
Area: Longboat Key
If you like to be on the water this newly upgraded Country Club Shores home has outstanding views of Sarasota Bay. Be the first to experience this comfortable open-concept home, one in from the bay, with fabulous water views that begin as soon as you step in the front door. It’s newly furnished and decorator designed from top to bottom, complete with 4 flat screen TV’s; three full updated baths; hard wood floor and vaulted 10 foot ceiling in living area; circular drive two car garage; boat dock; heated pool and spa; walk to gulf beach on deeded right of way. The understated exterior belies what is found inside. This home is located at the southern end of Longboat Key with very close proximity to St Armands Circle shops and restaurants. 
1945 Gulf of Mexico Dr. #307
Area: Longboat Key
GREAT Longboat Key location. This 2 bedroom, 2 bath condo has been totally updated. A southern exposure offers a partial view of the Gulf of Mexico from the screened balcony. HD flat screen TVs, wireless internet. Seaplace offers 2 swimming pools, Har-Tru tennis courts and a fitness center. A very short distant to St. Armands Circle & downtown Sarasota, for shopping, great restaurants and the theatre. Available for a seasonal rental. LUXURY, GULF OF MEXICO SARASOTA VACATION RENTAL.
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.
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.

4401 Gulf of Mexico Drive, #1001
Area: Longboat Key
Updated Gulf front corner unit with breathtaking views gulf to bay from this beachfront condo. Community features a fitness center, game room concierge, and community pool on the beach.
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).

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