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 80
Name
Area
Description
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. 
1257 S. Portofino Drive #107
Area: Siesta Key
This 55+ community is ideal for your winter vacation. Enjoy your morning coffee from the lanai over looking the intercostal. Amenities include direct beach access to Siesta Key beach, the #1 beach in the USA, community pool and spa, sauna, fitness, shuffleboard and walking distance to shops, restaurants and entertainment. Close proximity to the Stickney Point bridge enables easy access on and off the Key. 
3434 Casey Key Road
Area: Casey Key
Fabulous Gulf to Bay property on beautiful Casey Key, one of the most unusual keys on the West Coast of Florida. Immaculately kept three bedroom home with a dock on the bayside of Casey Key. Cabana across the street overlooks the Gulf of Mexico. Beautiful views from the living room across the pool to the bay. Updated kitchen with granite countertops and stainless appliances. Master bedroom has a king, first guest bedroom has a king and second guest bedroom has twins. Master bathroom has a tub and shower, 2nd bathroom has a shower only and the 3rd bathroom has a tub. The rent is $15,000 a month for season which is December 1- April 30. $8,000 per month off season months May 1 through November 31. CASEY KEY, GULF TO BAY, BEACH, VENICE, SARASOTA
1350 N. Portofino Drive #309
Area: Siesta Key
You will love this updated 3rd floor turnkey furnished unit with gorgeous Intracoastal and Harbor views. Siesta Harbor is surrounded by the Intracoastal Waterway with a boat harbor and deeded boat slips which can be leased for a nominal fee. This 55+ community is ideal for your May through December vacation with easy access on and off Siesta Key. Just a 1/4 mile from the Stickney Point bridge, shopping and restaurants are within easy walking distance. Beach access is directly across the street. Siesta Harbor offers a community pool and spa, numerous activities including a fishing club and social events in the clubhouse. No smoking and no pets please.
3708B Sandspur Lane
Area: Casey Key
The Banyan House is nestled among the trees on beautiful Casey Key. This is the main three bedroom house with a two bedroom cottage attached. Both properties can be rented together and would be a 5 bedroom house. This half is a two story beach house with a hot tub on a deck overlooking the private gardens. Enjoy this hideaway in the center of Casey Key down Sandspur Lane. There is a community day dock for a boat or canoe tie up, sit and watch the birds from this beautiful spot on the ICW. A short walk past a couple of houses brings you to the private beach and all the peace and solitude that offers. Three bedrooms upstairs with one bathroom upstairs and powder room downstairs. CASEY KEY, BEACH COMMUNITY, SARASOTA, VENICE.
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.
1100 Ben Franklin Drive, #305
Area: Lido Key / St. Armands Key
Beautifully decorated condo in Sarasota Florida right on Lido Beach.  One bedroom, with one and one half bathrooms located a short walk from St. Armands Circle.  Lido Surf and Sand is located right on the beach with a beautiful pool and spa.   One month minimum.
3203 Casey Key Road
Area: Casey Key
Get away to the privacy of the Casey Key beach, and an unusual retreat nestled right on the sand dunes. Master suite is on the second floor with views south down the beach and direct across the Gulf of Mexico. This Master Bedroom features his and hers bathrooms. On the main living area there is a second bedroom and office with a pull out bed. Available immediately for the summer.  No pets. 
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.
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
131 Garfield Drive, 4C
Area: Lido Key / St. Armands Key
Lovely top floor unit in The Riviera of Lido Beach with two bedrooms two bathrooms located in the heart of Lido Key. It is a few steps from the beach, and the Lido Pavilion. Nicely furnished with all the comforts of home and this unit has a large porch that overlooks the tree tops with a view of downtown Sarasota in the distance. It is a short walk from St. Armands Circle, and a quick drive to downtown Sarasota. 
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. 
8630 Midnight Pass Road #A507
Area: Siesta Key
This gorgeous, totally renovated 2-bedroom 2-bath condo boasts stunning full Gulf of Mexico views. Enjoy coffee each morning on your top floor lanai or relax with a glass of wine and sunsets each evening. Every inch of this spacious open plan luxury condo has been remodeled with high-end finishes including; beautifully tiled bathrooms, stainless steel kitchen appliances, granite counter tops and custom cabinetry. No home away from home detail has been overlooked. The property is steps to the secluded sandy Gulf beach and has a cabana for your individual use. Heated pool and intercostal-side dock (for fishing, paddle boarding or kayaking) add to the list of amenities. The property is walking distance to Turtle Beach restaurants and a short trolley ride (which stops in front of the property) to both of Siesta Key’s villages. The unit is available for season and off-season. Laundry facilities are conveniently located on the same floor.
1102 Ben Franklin Dr, #514
Area: Lido Key / St. Armands Key
Great location on Lido Beach, within walking distance of the Circle. This two bedroom, two bathroom condo has fabulous north beach views. One month minimum. Perfect Florida vacation property with a community pool/hot tub right on the beach.  
19 Whispering Sands Dr. #805
Area: Siesta Key

Enjoy this great view of the gulf from this 2 bedroom, 2 bath condo on the 8th floor. Condo has been remodel with granite kitchen counter tops, built in cabinets in master bathroom and tile floor. You can walk out of the building directly to your own private beach. This unit is walking distance to the Siesta Key village, where you can enjoy your morning coffee and a great meal at one of the local restaurants. Sit on your lanai and enjoy a beautiful sunset.


Showing Results 1 - 15 of 80