Southwest Florida Island Vacation Rentals

Jennette Properties offers luxury vacation rentals throughout all the islands on the Gulf coast including  the barrier islands Longboat Key, Lido Key, Siesta Key, Casey Key and much more. Our beautiful vacation rental properties are surrounded by top rated beaches along the Gulf.  
 
If you're looking for the best beach vacation rentals in Florida, check our inventory of properties available.


Showing Results 1 - 15 of 89
Name
Area
Description
35 S. Washington Drive
Area: Lido Key / St. Armands Key
SARASOTA'S JEWEL ST ARMANDS KEY ** LUXURY FURNISHED FOUR BEDROOM HOME AVAILABLE FOR MONTHLY LET. This stunning home with spectacular views over Sarasota Bay is ONE OF A KIND. Location! Location! Location! Walk to St. Armand’s Circle and Lido beach and convenient for Sarasota's downtown. Impressive three story home and in a class all its own with impeccable craftsmanship and attention to detail. From the Living room and gorgeous kitchen with top of the range Stainless Steel appliances you can walk out onto your 30 ft. balcony with outdoor grill and look out over your pool and Sarasota Bay and beyond. You even have a lovely wet bar with additional appliances so a wonderful home for entertaining. The generous sized Master Suite with exquisite en-suite bathroom will not disappoint with private balcony where again you can enjoy the natural beauty of the waterfront. All guest bedrooms have en-suite bathrooms. In addition, the home offers a study with custom mahogany built-in cabinetry, the essential ELEVATOR and 4-car garage. An oversized game room with French doors lead directly onto the patio with sparkling pool and spa. The private back yard with deep water dock and jet ski lifts makes the perfect setting for your RESORT WATERFRONT retreat GET AWAY.
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.
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.
5663 Midnight Pass Road #407
Area: Siesta Key
Enjoy all that Siesta Key has to offer at White Sands Village across from world famous Siesta Key Beach! This two bedroom two bath unit is located on the ground floor with partial views of the Intracoastal and steps to the heated pool! Washer and Dryer in unit. Community heated pool at clubhouse. King beds in both bedrooms. Public tennis courts at the beach directly across the street. Assigned covered parking.
2901 Casey Key Road
Area: Casey Key
Welcome to Villa di Tramonto, house of sunsets, gorgeous remodeled 4 bed 4.5 bath home complete with private beach on the Gulf of Mexico. Stunning views on all levels, this magnificent home is decorated in elegant coastal furnishings. Entering the front door from the gated and beautifully foliaged entryway immediate ocean views are offered along with a sitting area, guest suite with mini kitchen, full bath and washer/dryer. Take the elevator or the inviting staircase to the spacious living areas. The custom kitchen and large dining area overlook the beach, the living room with game table and large flat screen TV and the office/den with custom cabinetry all offer stunning sunset views. The master suite and two en-suite bedrooms are on the top floor as well as a trundle/day bed on the landing for extra sleeping. The house includes marble floors, custom built in cabinetry, two wet bars, two sets of washer and dryers plus a foldout queen sofa bed on the ground floor. Relax in the living room with the windows open or on one of the two gulf -side terraces and take in the sound of the waves or watch dolphins go by. Two car garage, ample storage, an elevator, heated pool and spa complete the amenities. A private path leads to the deeded dock on the bay side for kayaking or bird watching. Casey Key destination is the ultimate spot in beach living on the West Coast of Florida, private beaches, but short distances from dining and stores. Convenient to I-75, Venice and Sarasota. 
231 Garden Lane
Area: Siesta Key
SIESTA KEY TROPICAL PARADISE great FAMILY HOME Right by the beach. North Siesta Key near the north bridge for easy on-and-off island access. Elegance and functionality in this updated, gated, North Siesta Key estate just across the street from inviting Shell Beach on the Gulf of Mexico and set on a very private road. The sparkling pool and spa are absolutely perfect. Relax inside or out on the large, covered porch. The main floor features a grand entryway, a large open-concept living and dining room, a cook's kitchen featuring a breakfast bar with top-of-the-line appliances, a bedroom with adjoining office/den and an adjacent full bath. Two guest bedrooms with a Jack and Jill bath and a pool bath. Venture up the showpiece staircase and go right to the master suite or go left to an oversized bonus room or fourth bedroom. With nearly 4,300 square feet of living area, there is plenty of room for all to ENJOY THE SARASOTA LIFESTYLE FOR A WEEK OR LONGER STAY. Minutes to the Siesta Key BEACHES & Village with shopping, restaurants, and entertainment.
1 Ben Franklin Drive #22
Area: Lido Key / St. Armands Key
Gorgeous condo available for season or an annual lease, in what must be the best location on Lido Key. Fresh and light decorating to put you in a vacation state of mind and enjoy the views from the condo of the swimming pool, palm trees and the Gulf of Mexico! This condo has it all, the beach and St. Armands Circle in its own backyard! All tile floors, updated kitchen with all the comforts of home, two bedrooms and two bathrooms. SEASONAL or ANNUAL RENTAL, BEACH, SARASOTA, LIDO KEY, ST. ARMANDS.
3999 Casey Key Road
Area: Casey Key
Gorgeous private gulf front hideway on exclusive Casey Key.  Deck overlooking private beach.  If you like island living this is the one for you! Two bedroom, two bathroom cottage, decorated in bright colors.  Very private. Close to Sarasota, Venice and convenient access to I-75.  Within walking distance to Blackburn Point bridge and restaurant. Florida beach living at its best! One month minimum.
1257 Tree Bay Lane
Area: Siesta Key
Expansive four bedroom home on the water on South Siesta Key is available for season 2017. Through the entrance on the first floor you enter into the family room with views of the pool and intracoastal waterway. There is also a bedroom and private bathroom on this level. Up the open staircase leads to the main living floor with a skylight over the open plan kitchen, dining room and living room. All of these rooms overlook the pool and the intracoastal waterway. The master bedroom also has a comfortable sitting area and also a water view, the master bathroom features a large tub and separate shower, with double sinks. All bathrooms have been recently updated, and the bed sizes in all the remaining bedrooms are queen sized. The house also has 2 sofa beds, perfect for extra guests. There is a dock at the house and the beach access is a short distance. Available for Season. SINGLE FAMILY HOME SIESTA KEY SARASOTA FLORIDA SEASONAL RENTAL
1232 Solitude Lane
Area: Siesta Key
Siesta Key luxury water front home ready for the 2016 season. NEW CONSTRUCTION. THIS 5 BEDROOM, 4 BATH FAMILY HOME ON A PRIVATE DEAD END ROAD MAKES THIS LOCATION A GREAT PLACE FOR THE FAMILY TO PLAY AND ENJOY THIS NEW HOME ON SAILBOAT WATER, WALK TO THE POWDER SANDY BEACH OF SIESTA AND VILLAGE. . THIS RELAXED LIVING HOME HAS LARGE BEDROOMS.......LARGE KITCHEN AND SEPARATE PANTRY, STORAGE CLOSET THAT CAN ALSO BE USED FOR A WINE CELLAR...CENTRAL VAC SYSTEM,CENTRAL ALARM, HEATED POOL WITH POOL BATH ...VIEWS.....BOATING IN YOUR BACKYARD....ELEVATOR...3 CAR GARAGE, OUTDOOR SHOWER NEW SEA WALL CAP, BEAUTIFUL LANDSCAPING WITH LED GROUND LIGHTING. THE MOMENT YOU ENTER THE HOME YOU WILL FEEL THE QUALITY CONSTRUCTION. A MUST SEE. THIS IS THE PERFECT WINTER GET-A-WAY!
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).
2100 Ben Franklin Drive #102
Area: Lido Key / St. Armands Key
Cute one bedroom condo on the first floor of Lido Harbor South. King sized bed in the master bedroom, and fold out couch in the living room. Just steps away from the swimming pool and located right on Lido Beach. Conveniently located near the parking space, so no steps or elevators. Located a short drive from St. Armands Circle and downtown Sarasota. LIDO BEACH, SARASOTA, FLORIDA, BEACH CONDO.
435 L'Ambiance Drive #807
Area: Longboat Key
Stunning unit behind the gates in sought after Longboat Key. The L'Ambiance is situated on 18 acres on the beautiful sandy beaches of the Gulf of Mexico. The residence is an expansive 2 bedroom, 3 bath unit on the 8th floor with 270 degree views over the Gulf of Mexico, Sarasota Bay, the lush green golf courses of the LBK Club and Sarasota Skyline. Accessed on a private elevator the apartment is 2500 square feet plus a wrap around terrace adding an additional 1000 sq feet. It offers a master bedroom with double bathroom, guest bedroom with full bath, powder room, living room, den dining area and eat in kitchen. Sunrises, sunsets the apartment is bathes in light all day long through floor to ceiling windows in all rooms. The condominium itself sits directly on the beach with a magnificent pool, Jacuzzi, tennis courts, sauna , steam room, gym, running track. pool room, reading room and last, but not least, the Wine Cellar! Perfect for your long term, annual, or seasonal rental!
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.
4532 Ocean Blvd. #201
Area: Siesta Key
SIESTA TOWNHOUSE DIRECT GULF FRONT - Spectacular views of the Gulf of Mexico. This completely renovated TURN KEY FURNISHED two bedroom end unit town house is totally modernized and absolutely perfect. Available for your IN Season stay for three months or longer. Just a very short walk to Siesta Village and Beaches. This 20 unit complex is set back on Ocean Blvd. on a large private lot for complete privacy and quiet. Master Bedroom with a picture window overlooking Gulf of Mexico and on the first floor sit back and enjoy the water views of the dolphins. Private pier /dock for fishing or enjoying life on the Gulf.

Showing Results 1 - 15 of 89