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 30
Name
Area
Description
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. 
2109 Gulf of Mexico Drive #1402
Area: Longboat Key
LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with ease. Enjoy shopping on St. Armands Circle, downtown Sarasota or on the key. South end of Longboat Key makes for easy access anywhere you want to go. Plenty of restaurants to choose from, from the key to downtown Sarasota. VACATION, LUXURY, GULF OF MEXICO, SARASOTA FL. RENTALS.
6945 Gulf of Mexico Drive #11
Area: Longboat Key
Listen to the waves right outside your lanai from this direct beachfront condo on Longboat key. This condo has been beautifully furnished with everything new just this past year. Condo overlooks beach and heated pool just steps from the back porch. Enjoy your morning coffee on the screened lanai with the peaceful sounds of the seagulls and the water and the relaxing salty breeze. Small community sits back in secluded privacy but is conveniently located to shops and restaurants all along Longboat and with St. Armands circle on one end and Anna Maria on the other. King sized bed in master with doors opening to the oversize screen lanai, two twins in guest room. Flat screen TV's, internet included. Short term, vacation rentals, Longboat Key, beach rentals, Sarasota rentals, Gulf of Mexico beach rental. WELCOME to PARADISE!!!!
 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.
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.
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. 
2425 Gulf of Mexico Drive, #4E
Area: Longboat Key
LONGBOAT KEY, this two bedroom, two bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award-winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen. A five minute walk to shopping & pharmacy. Short drive to St. Armands Circle or downtown Sarasota, for restaurants & theaters. SARASOTA FL, BEACHFRONT, GULF OF MEXICO, LUXURY, SEASONAL RENTAL.
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.
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.
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.
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
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).
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.
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.
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.

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