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 27
Name
Area
Description
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.
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.
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. 
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.
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.
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
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. 
640 Longview Drive
Area: Longboat Key
Come experience beautiful Longboat Key AND a serene California vibe in this totally remodeled modern home with many builder upgrades! Situated on Longboat Key sailboat water with no bridges to Sarasota Bay and the sparkling waters of the Gulf of Mexico, this peaceful and private sanctuary with 3 bedrooms and two baths has a large boat dock with room for your sailboat up to approx. 24' long. From your boat the oversized terraced deck with outdoor seating and gas grill welcome you after a day out on the water. The spacious indoor floor plan allows for entertaining, relaxing, and family fun. The kitchen has updated appliances, granite countertops and gas stove. The two larger bedrooms are split plan and the master bedroom has a generous sized walk-in closet, all new private bath and opens out to the pool and water. The open pool, oversized deck and lush mature landscaping really lend themselves to that peaceful, easy feeling you long for when getting away from it all. There is a two car garage with plenty of room for storage and a circular driveway for additional vehicle. Located mid-key on Longboat, the beautiful Gulf of Mexico beaches, shopping, dining and Publix are all within your reach. St. Armand's Circle, and all the culture and nightlife that Sarasota has to offer is also so close by. The Buttonwood community also offers well maintained community tennis courts and plenty of bird watching while nature's beauty surrounds you. Refresh your mind and body in this wonderful Longboat Key home. Owner will consider a pet under 40 lbs or under. There are seasonal rates on this listing so please call for most accurate rate quote on your particular stay.
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.
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 .
1095 Gulf of Mexico Drive #502
Area: Longboat Key
This gulf front unit has been completely renovated top to bottom. Offering gorgeous views of the gulf with stunning sunsets. Stainless steel appliances, tile wood plank floors, beach décor, top notch throughout & Everything is NEW. Beach Place is located on the south end of Longboat Key. Go for an early morning stroll with your coffee on beautiful sandy beaches that stretch for miles. If your looking for a sunset, enjoy them nightly on your terrace with a cool glass your favorite. This unit is booked for Season 2019 (Jan - March) but available for a quick summer or fall Get-A-Way. 30 day minimum.
 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.
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.
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.
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.

Showing Results 1 - 15 of 27
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