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
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
6285 Midnight Pass Road #107
Area: Siesta Key
Come and relax in this bright end unit condo. This 2 bedroom 2 bath condo has its own washer and dry. The master bath has just been completed updated. The complex has a community room and exercise room on bayside/game room/2 lighted tennis courts/pickle ball courts. Private beach access, heated swimming pools, saunas, spas, outdoor grills, showers and picnic areas. Enjoy your morning coffee on the lanai with partial view of intercostal. Condo available now till Dec 31, 2017 for two weekly rental or monthly. Owners uses condo in Season.
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.
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..
3630 Gulf of Mexico Drive #301
Area: Longboat Key

LONGBOAT KEY..This three bedroom, 2 bath corner unit has both full GULF VIEWS from one screened balcony for watching gorgeous sunsets after a day at the beach and, full BAY VIEWS from the second screened balcony. Kitchen and bathrooms have been newly renovated with granite counters. Beautiful new tile flooring installed on the diagonal makes this unit feel even larger than it is and new carpet in the bedrooms. Full sized laundry room in the unit. Just a few steps across the street is a PRIVATE BEACH for Buttonwood residents. The private boat slip on SARASOTA BAY assigned to this unit will accommodate a 30' boat. Enjoy the amenities available for your use, TENNIS COURTS, RACQUET BALL COURTS, club house overlooking the BAYFRONT HEATED POOL. Glass doors enclosing the balcony allows this large room to be used as a FLORIDA ROOM in all weather. Extra storage for bikes. Mid-key location is very convenient to shopping, restaurants etc. This unit is also being offered as an annual.

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.
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.
1975 Gulf of Mexico Drive #302
Area: Longboat Key
Meticulously maintained loft condo in desirable G4 beachfront building. Accommodates up to 4 guests. This is the owners second home and is not a typical rental. An open and airy gr3eat room with vaulted ceilings. Completely remodeled and tastefully decorated with Ethan Allen furnishings and original artwork. Granite and Stainless in the fully equipped gourmet kitchen. The master bedroom is spacious with generous closet space. En-suite Washer/Dryer, Blue Ray, Two TVs, DVD WIFI access, HP Printer, large lanai with garden and tennis court views. If you are looking for a beautiful immaculate rental this is a must see. 
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.
1208 Solitude Lane
Area: Siesta Key
Fantastic house on Siesta Key near the village and the world famous beach. Three bedrooms plus office and upstairs loft. No elevator. Relax on the porch watching a flat screen TV overlooking the pool/spa and canal. Lift and dock.
3509 Casey Key Road
Area: Casey Key

 Gorgeous luxury home, one of the finest Gulf to Bay properties on Casey Key, lovingly furnished for comfortable stays on the beach.  Wander from the house to the private beach and your own cabana to watch the sunset from. The house is on the bayside with views from the house across the pool and the bay.  House has a master bedroom on the ground floor and it is handicap accessible.  Other bedrooms are upstairs, in this wonderful Casey Key property. 1 month minimum. 

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.
1640 Summerhouse Lane #10
Area: Siesta Key
Arrive in style in your own private elevator to this luxurious condo on sought after Siesta Key. This condo boasts 3 bedrooms, 2 1/2 baths and over 2200 sq feet and is located behind the gates at Summer Cove. This luxurious condo has been professionally decorated. The amenities include state of the art fitness center, billiards room, community center, heated community pool, dock and most importantly access to the World Famous Siesta Key Beach located directly across the street! 20 minutes to downtown Sarasota with all that has to offer. Fine dining, boutique shopping, the arts, opera etc. Also walking distance to Siesta Key Village which is always a fun time. Located on the south end of the key is perfect as it offers easy access to and from the Island. This is the perfect spot for your winter get-away!
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 .
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!

Showing Results 1 - 15 of 98