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 28
Name
Area
Description
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.
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. 
 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.
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-Mar 2019. Available now through the summer and fall.
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 .
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.
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
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.
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. 
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.
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
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.
3160 Bayou Sound
Area: Longboat Key
SARASOTA LONGBOAT KEY WATERFRONT HOME @ BAY ISLES. This stunning home is located behind the gate of Bay Isles on the Bayou Sound. The spacious screened lanai is great for entertaining and relaxing. A sparkling pool and spa overlooks a private and peaceful Lagoon with a serene natural view of the trimmed mangroves on a meandering waterway to the Sarasota Bay. Many beautiful nature sights to enjoy of birds nesting and abundant fish. Three well appointed bedrooms in a SPLIT PLAN: Master Bedroom with a CALIFORNIA KING size bed, and KING bed and Queen Bed in the Guest Bedrooms, in this well designed split floor plan home. Walk in the front door and you are welcomed by a beautiful tropical view of the pool and the Lagoon beyond. Step down Living Room with a soaring marble fireplace and built-in bar. The master bedroom suite attaches to its own glass atrium and a luxurious master bathroom with a walk in shower and jetted soaking tub. Private Beach Club for Bay Isles on the Gulf of Mexico minutes away by car. Beach Club Facilities include: restrooms, showers, kitchen facilities, BBQ cook out area with picnic area. Five minute WALK to Publix Grocery and CVS pharmacy. 24/7 manned GUARD GATE. Many scenic walking paths to Longboat Key Marina, Golf Course and Tennis Club. Mature landscaping and trees create a Tropical paradise environment to Enjoy Paradise in a very PEACEFUL setting.
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..
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.

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