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 98
Name
Area
Description
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!
1935 Gulf of Mexico Drive #211
Area: Longboat Key
SEAPLACE on Longboat Key. Enjoy the wonderful GULF OF MEXICO WATER VIEWS from this THREE bedroom, two bath CORNER UNIT condominium. TURN KEY FURNISHED available. Remodeled bathrooms and kitchen. Two terraces overlooking the Gulf of Mexico. Seaplace amenities include two pools with hot tubs, fitness center, Har-Tru lighted tennis courts, BBQ grills, club house, and fitness center.
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 $12,000 a month for season which is December 1- April 30. $7,000 per month off season months May 1 through November 31. CASEY KEY, GULF TO BAY, BEACH, VENICE, SARASOTA
2050 Ben Franklin Drive A 602
Area: Lido Key / St. Armands Key
Exquisite condo available for 2016 season in the Orchid Beach Club on Lido Key, Sarasota, Florida. Professional decorating in every room to perfection at the highest level of good taste. Private elevator leads you into the marble foyer, which then leads to the living room, dining room and large porch overlooking Lido Key, downtown Sarasota in the distance and also the beach on Lido Key. There is also a family room in this spacious meticulously maintained designer home. Large gourmet kitchen, and dinette area with huge views and gas barbeque grill just steps away on the expansive porch. The master bedroom features a king sized bed, and the second bedroom suite features a king sized bed also, all bedrooms have spectacular views. The third bedroom and bath is also set up as an office with a fold out queen sized sofa bed. All the bathrooms are exquisitely appointed with marble tile and glass shower enclosures. The upgrades are too numerous to mention, but if you want privacy, the beautiful Orchid Beach Club is for you. Just minutes from St. Armand's Circle and downtown Sarasota. ORCHID BEACH CLUB, LIDO KEY, SARASOTA, FLORIDA.
3708 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.
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-March 2017. Available now through the summer and fall.
2295 Gulf of Mexico #115
Area: Longboat Key
LONGBOAT KEY...ISLANDER CLUB. Two bedroom, two bath condo directly on the beach with a view of the Bay, Bay Isles wooded area and the Golf course. Open floor plan, living room dining room combo. There are sliding glass doors in all the rooms that lead to the covered patio area. Plenty of closets and storage space. On site management staff. Amenities include an Olympic size pool on the beach. Fitness center and elegant community room both facing the ocean. Two lighted tennis courts, billiard room, sauna, library and two fishing piers. Close to shopping, restaurants, St Armands Circle and downtown Sarasota. LONGBOAT KEY, SARASOTA, VACATION RENTAL, LUXURY.
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.

105 Seagull Lane
Area: Bird Key
Serene and spacious modern style 4 bedroom/3 bath home on exclusive Bird Key now available for seasonal or annual rental. This wonderful space has been totally renovated; kitchen and baths all new throughout, brand new decorator turnkey furnishings. Live the Bird Key lifestyle! This home has spectacular views of Sarasota Bay and Bird Key Park. Easy access to walking trail to and over the Sarasota Ringling Bridge. Get some great walking in surrounded by fabulous Florida water and views. The heated pool/spa area has fountains and a rock waterfall, grilling area and water views. The open floor plan allows for easy entertaining and offers a light and bright space for relaxing in style. There are water views and a wood burning fireplace in both the living area and the master bedroom. The Bird Key location is so convenient to shopping and dining on St Armand's Circle, Lido Beach and all the culture and nightlife that downtown Sarasota has to offer. Seasonal or annual rentals considered.
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. 
322 Bird Key Drive
Area: Bird Key
Single family home on desired Bird Key for rent. This spacious garden home has 2,030 square feet, three bedrooms, two bathrooms, a large living room/dining room combination, separate family room, caged lanai as well as an outdoor area for entertaining. The master bedroom has a king sized bed, second bedroom has a queen bed and third bedroom has been set up like an office with a desk but does have a twin bed for guests. The home has a two car garage (only one spot available). Wide open for season 2017. Two month or longer bookings only due to association rules. Bird Key association approval fee is $600.
156 Siesta Drive
Area: Siesta Key
Unique FURNISHED home available for rent on Siesta Key. This single family home has four bedrooms, three bathrooms, living room, family room, kitchen with dining area, breakfast bar, two bedrooms on the second level loft, laundry room, spacious deck with two sitting areas, private pool and two car garage (ONLY one space available). The living space is on two levels with stairs to both and NO elevator. Master bedroom has a king sized bed, walk in closet, en suite bathroom with double sinks and a stall shower. Bedroom two and three have queen sized beds and bedroom four has two twin beds. First guest bathroom has a tub/shower combination and the second has a stall shower. Laundry room and third bathroom are on the garage level all other living areas on the second and third levels. Home is available for an annual or short term rental. Short term rentals must be month long or longer. Small pet allowed with the owner's approval. Available immediately.
4632 Ocean Blvd.
Area: Siesta Key
Island Lifestyle right on the Gulf on Mexico in this gorgeous estate available for longer term rentals. Loads of charm and history in this house situated down a long private driveway off Ocean Boulevard. The house has been lovingly restored. Walk into this house and immediately the charm of the home is evident. There is a separate living and dining areas each with their own fireplace, an eat in kitchen plus an additional family room. The master suite is on the ground floor, and from the bed it is possible to look across the Gulf of Mexico with unobstructed views. All three bedrooms upstairs are en-suite. The main house is next to the water with two stories and some of the bedrooms are upstairs. There is a recreation room/apartment with a separate kitchen and bathroom on the opposite side of the pool in the unique cabana. Perfect as the pool cabana, rec room or just extra space from the main house. The pool is private with a raised breezeway along the side and perfect for exercising and play. Behind the cabana is the covered parking space. On the property there is a sea wall and a fishing pier. This home is located on the north end of Siesta Key just a short distance from the world renowned Siesta Kay beach with shopping and restaurants of the Siesta Key Village. SINGLE FAMILY HOME, SIESTA KEY ON THE GULF OF MEXICO!!
  
1300 Ben Franklin Drive #302
Area: The 'Ritz-Carlton'
This is a gorgeous 2 bedroom 2 bath condo at the Ritz Carlton Beach Residences. The property is spacious at over 2300 sq. feet. Light bright and airy with partial views of the Gulf of Mexico. This condo is being completely remodeled in April by a professional decorator. The Ritz Carlton Gold Membership is fully transferrable and entitles guest to access to the Ritz Carlton Tom Fazio Golf Course, the Ritz Carlton Members Club, the spa and the fitness center. The Ritz Beach Residences also boasts its own private pool, billiards room, movie theater, gated security, 24 hour concierge service, room service and much, much more. Come enjoy The Ritz Carlton and Florida living at its best!
5880 Midnight Pass Road #508
Area: Siesta Key
Enjoy the beautiful sunset from this 5th floor condo. This 2 bedroom 2 bath condo has been freshly painted and all new furniture. The condo is located on the Gulf side of Siesta Key. This community has private pool, tennis court and small fitness room. Walk through the beautiful court yard to your own beach. You can take a leisurely walk to the public beach as well as take the free taxi rides to Siesta Key Village for the nightly dining and music. Unit is available for season 2018.

Showing Results 1 - 15 of 98