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
1640 Summerhouse Lane #10
Area: Siesta Key
Arrive in style with your own private elevator into your foyer. This spacious condo is light and bright with a southern exposure. Entertaining and relaxation is at its finest with a huge bricked terrace serving a table for eight plus 2 lounges. Beautiful glass dining table. All upscale appointments in a contemporary bldg ready for you to explore world famous Siesta Key. Master bedroom has king sized bed, LR has HS internet, DVD. & leather sectional. Kitchen has stainless, granite and open bar with stools. Like new condition.
1250 N. Portofino Drive #301
Area: Siesta Key
Siesta Harbor is a 55+ community overlooking Sarasota's Intracoastal Waterway. This south-facing end unit features two bedrooms and 2 baths with a King in the Master and twins in the guest bedroom. The community laundry room/storage room is next to the elevator. Cable, phone and Internet are included with the rental. Boat slips right outside your door are available for a nominal fee. Deeded beach access across the street. The community offers social events and card games for winter guests with full use of the clubhouse, sauna, fitness, heated pool & spa and shuffleboard court. Take a short walk to the south village for shopping and dining or hop on Jonny's free rides for a short trip to the public beach or Siesta Key Village for more entertainment and fun. Relax on your lanai with your morning coffee and watch the boats go in and out of the Harbor. No pets allowed.
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.
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. 
5911 Midnight Pass Road #103
Area: Siesta Key

Stunning 2bdrm./2 bath condo situated on Siesta Key, steps to the beach this newly renovated condo has views of the dock and bay, private boat slip will accommodate up to a 50' boat, gourmet kitchen with new appliances and designer furnishings. No pets allowed. Available off-season, call for High Season Prices 

1112 N. Casey Key Road
Area: Casey Key
Island Living at it's best! This beautiful home has been featured in several National publications. It is located in the private section of beautiful Casey Key on the north end. It has a breathtaking private beach and frontage on the bay with views of the Intracoastal Waterway from the back deck with a built in fire pit. This magnificent home has 4 bedrooms and three bathrooms, plus a guest powder room. On the main floor, with an open plan, the state of the art kitchen is equipped with upscale appliances, and opens up to the living areas that overlook the bay. There are flat screen televisions with cable in each of the bedrooms as well as in the main living room, and the game room. The game room is separate from the rest of the downstairs living areas, on the beach side of the house. The Master suite is located upstairs on its own private floor, with endless views of the tranquil blue waters of the Gulf of Mexico, it features a king sized bed. The master bathroom has a marble walk in shower and spa-like cast iron soaking tub. The house has large windows and high ceilings with lots of natural light. CASEY KEY, SARASOTA, VENICE, BEACH FRONT SINGLE FAMILY HOME, VACATION RENTAL.
231 Garden Lane
Area: Siesta Key
Wow!!:::Spanish Mediterranean beauty available for season. Almost 4300 sq.ft. open plan, high ceilings with 4 bedrooms, 5 baths, neutral tile, granite counters, hardwood cabinets and floors, double stairway, huge media room and outdoor deecks overlooking tiled pool & spa. 2 bedrooms, + 3 baths, and office downstairs. Master retreat and media room and 2 full baths upstairs. Gorgeous home available long or short term.
601 S. Blvd. of the Presidents
Area: Lido Key / St. Armands Key
Enjoy your stay on Sarasotas Lido Key in this lovely home located 1 block from the beach, community pool and famous St. Armands Circle. This spacious home also has a den office and will allow a small dog
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.
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 .
1300 North Portofino Drive #S208
Area: Siesta Key
Turnkey furnished annual rental on Siesta Key at Siesta Harbor, a 55+ community. This 2nd floor corner unit has beautiful views of the harbor and the Intracoastal Waterway. Boat slips available to renters. 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. Move right in to this turnkey furnished 2 bedroom unit with gorgeous harbor views. Laundry room is on the same floor.
1800 Ben Franklin Drive #907B
Area: Lido Key / St. Armands Key
LUXURY the beautiful L'Elegance on LIDO BEACH. This updated condo has 2 bedrooms + a den, 3 full baths. Beautiful wood flooring in the living-dining area and continues into the den and kitchen with breakfast area. Enjoy sweeping city, bay and partial Gulf views from this ninth floor condominium. Kitchen has granite counters tops and stainless steel appliances. Wrap around terraces facing east & north open to the living area, kitchen and master bedroom. Directly on LIDO BEACH L'Elegance with Gulf side pool, hot tub, two tennis courts, fitness center and card room provides for the perfect vacation, resort living. Minimum rental period with HOA is 3 months. This unit is available starting January 1, 2017.
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. 
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.
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.

Showing Results 1 - 15 of 98