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 88
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 .
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
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
105 Seagull Lane
Area: Bird Key
ocation!Vacation!Location!If you want to feel like you're always on vacation then you've come to the right home & neighborhood! This modern masterpiece is located on the sought after Bird Key. This home has extraordinary water views that greet you on your arrival and are absolutely breathtaking from almost every room. This home has a wonderful floor plan, w/exceptional bright/natural light & high ceilings. 4 bedrooms,3 full baths,separate laundry room & tons of storage.Travertine flooring, gourmet kitchen w/top of the line appliances, and granite . The bathrooms have been recently updated, new automatic blinds & awnings, interior paint, light fixtures & custom closets.New landscape w/a beautiful mix of palms, flowering bushes & other low maintenance tropical plants. Large pool/spa. Spend your days in the sun, or head out for a stroll or bike ride to the local hot spots: St. Armand's Circle, Downtown SRQ, Marina Jack etc.In the evenings, relax on one of the many terraces & look across at the wide open views of SRQ Bay.Full-time living or a vacation retreat, this 1st class home has it all!
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.
106 Beach Road
Area: Siesta Key
South Beach Miami Style House right on Siesta Beach! Ultra luxurious rental available for annual or longer term seasonal rental. Available immediately! Just steps away from Siesta Key Village and all the amenities it has to offer. On every level of this open floor plan home are unlimited views of the incomparable sand on Siesta Key and the Gulf of Mexico. Set in a tropical paradise of palm trees and lush vegetation, modern design with pops of color. Professionally decorated with beautiful furnishings and immediate move in is available. This attached multi level home has an elevator and under building parking. Step into the foyer and glass enclosed stair well plus elevator, the kitchen and family/dining open plan floor has a large porch overlooking the beach, as well as a bonus study/den. The kitchen features high end stainless appliances, large bar perfect for entertaining all overlooking the beach. Up another floor to more bedrooms and a family/game room on the top floor. This location is central on Siesta Key just a block or so from all that Siesta Key has to offer, perfect beach living!
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.
5519 Azure Way
Area: Siesta Key
Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car!!! 2 King/2 bunk beds /daybed , queen sleeper and space galore.
1095 Gulf of Mexico Drive, #101
Area: Longboat Key
Wonderful first floor walk out.  Direct Gulf views, pool and lake views.   This unit has been completely redone top to bottom.  Professionally decorated with 17 inch tile throughout, granite in the kitchen and bathrooms, maple cabinets throughout. Longboat Key/Vacation/Rental/Holiday
1102 Ben Franklin Drive #307
Area: Lido Key / St. Armands Key

Beautifully renovated unit. This unit has been redone top to bottom. The beautiful building sits right on the Gulf of Mexico. Enjoy easy strolls on the white sands of Lido Beach and to St. Armand's Circle which is just over 1/2 mile away. This unit has partial Gulf Views and a large lanai. This unit is available for a long or short term rental. A true must see! Lido Beach, Sarasota, Florida vacation rental.

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.
5525 Azure Way
Area: Siesta Key
Fabulous large home decorated to perfection just over 400 steps from Siesta Public Beach, one the of the best beaches in the world. House is large and has 5 en suite bedrooms. Enormous pool with lions head fountains and hot tub overlooking the wide canal. You can tie your boat up to the sea wall, and enjoy the outdoor eating area by a man made beach overlooking the canal. All the comforts of home for large family gatherings. House has two master suites one on the ground floor and second one upstairs. Beautiful landscaping in this fabulous Siesta Key home, convenient to the Siesta tennis courts and the village. Rentals of six months or less are subject to local and state taxes.
1300 Ben Franklin Drive #1106
Area: The 'Ritz-Carlton'
Incredible Ritz Beach Residences condo. Enjoy amazing views of Sarasota Bay, the Gulf of Mexico and the city of Sarasota from the condo windows and wrap around terrace. This professionally decorated 11th floor unit has 3 bedrooms, 3 bathrooms, 11 foot ceilings, travertine marble floors with throw rugs, split floor plan and a gourmet kitchen with granite counter tops and views of the water. The condo has a formal dining room, separate eating area off the kitchen, comfortable living room with a cocktail area and wet bar. The master bedroom, has breathtaking views of the Gulf of Mexico, a king sized bed, wet bar, large walk in closet, bathroom with double sinks, large shower and a garden tub. The first guest bedroom has a queen sized bed. The second guest bedroom is set up as an office with a desk and pull out sleeper sofa with a queen sized bed. You will have 24 hour concierge service provided by the Ritz Carlton. Amenities include two pools, spa, sundeck, a private Gulf of Mexico beach area to enjoy, social room, fitness center, billiard room, meeting rooms, library and movie theater. Membership transfer will allow privileges at a 72 par Tom Fazio golf course for your pleasure. Located just minutes from St. Armand's Circle and downtown Sarasota for theaters, shopping and fine dining. Utilities cap of $150 per month.
5238 Winding Way
Area: Siesta Key
Fabulous home in Siesta Key minutes away from the famous Siesta Key beach and the Village of Siesta Key. Gorgeous house with very private settings, features 3 bedrooms, 3 bathrooms, huge chef kitchen, open lanais on second floor with beautiful views of the preserve. Ground floor with enclosed lanai, car garage, storage for bikes, kayak and much more. Second floor boasts an open plan, bright and tranquil settings with amazing kitchen, open lanais and laundry room and 3rd bedroom. 3rd floor with guest bedroom and private bath, master suite with its own suite bathroom with double sinks, separate shower, tub, walk-in closet. Home is surrounded by lush tropical landscaping. Ride the bikes to Siesta Key beach, and explore what this amazing Island have to offer. Excellent location, private street, conveniently located close to the beach, Siesta Key village, downtown Sarasota, entertainment, shopping, golf and so much more. This is your absolute best vacation spot! Vacation rentals, Siesta Key, Sarasota, seasonal. Dogs OK. Welcome to Paradise!!! Once you are here.. you won't want to leave
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.

Showing Results 1 - 15 of 88