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 94
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. 
3708A Sandspur Lane
Area: Casey Key
Cute "Seagrape Cottage" available for a relaxing stay on Casey Key. Nestled in the center of the key just steps away from a private beach easement for solitude on the beach. Also steps away from a private path to a dock on the bay for fishing or relaxing. Screened porch with dining table, flat screen televisions in Living Room and Master Bedroom, wi-fi included. This small cottage is attached to another house which is rented separately. Queen sized bed in Master Bedroom, two twin beds in second bedroom.
1 Ben Franklin Drive #22
Area: Lido Key / St. Armands Key
Gorgeous condo available for season or an annual lease, in what must be the best location on Lido Key. Fresh and light decorating to put you in a vacation state of mind and enjoy the views from the condo of the swimming pool, palm trees and the Gulf of Mexico! This condo has it all, the beach and St. Armands Circle in its own backyard! All tile floors, updated kitchen with all the comforts of home, two bedrooms and two bathrooms. SEASONAL or ANNUAL RENTAL, BEACH, SARASOTA, LIDO KEY, ST. ARMANDS.
2109 Gulf of Mexico Drive #1402
Area: Longboat Key
LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with ease. Enjoy shopping on St. Armands Circle, downtown Sarasota or on the key. South end of Longboat Key makes for easy access anywhere you want to go. Plenty of restaurants to choose from, from the key to downtown Sarasota. VACATION, LUXURY, GULF OF MEXICO, SARASOTA FL. RENTALS.
6945 Gulf of Mexico Drive #11
Area: Longboat Key
Listen to the waves right outside your lanai from this direct beachfront condo on Longboat key. This condo has been beautifully furnished with everything new just this past year. Condo overlooks beach and heated pool just steps from the back porch. Enjoy your morning coffee on the screened lanai with the peaceful sounds of the seagulls and the water and the relaxing salty breeze. Small community sits back in secluded privacy but is conveniently located to shops and restaurants all along Longboat and with St. Armands circle on one end and Anna Maria on the other. King sized bed in master with doors opening to the oversize screen lanai, two twins in guest room. Flat screen TV's, internet included. Short term, vacation rentals, Longboat Key, beach rentals, Sarasota rentals, Gulf of Mexico beach rental. WELCOME to PARADISE!!!!
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. 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.

2910 Casey Key Road
Area: Casey Key
Experience European elegance and sophistication at this stunning bayfront Casey Key residence, complete with deeded beach access. Idyllically sited along the gentle waters of Blackburn Bay and tucked along meandering mangroves, this residence designed by architect George Merlin showcases classic architectural design while maximizing waterfront vistas and privacy. The superb design is combined with masonry construction on concrete driven pilings, a hip roof design, Anderson windows and doors and full hurricane protection to complete this quality package. Located on highly coveted Casey Key and surrounded by mature landscaping, this completely walled property offers residents the exclusive tropical lifestyle only found on this island. Large-scale windows, French doors and sliders allow for grand views of both the Gulf of Mexico and Blackburn Bay, and open to wrapping terraces and private balcony areas. Brilliantly finished with crown molding, stone flooring and custom cabinets, this home has a soft and inviting interior that can easily support any design style. The more casual lower level features a large entertainment space with wet bar that opens to the expansive outdoor living area, where the refreshing pool awaits. Also located on the lower level is a secondary master suite, giving residents the option for long-term guests or a multi-generational living environment. Enjoy the best of waterfront living with private beach access and bayside boat dock with lift.
 700 Hideaway Bay Lane
Area: Longboat Key
Stunning Longboat Key family retreat. Modern and dramatic four bedroom Luxury custom home to enjoy the grand island style living with all the modern conveniences. Beautiful landscaped corner lot in Longboat Key's Hideaway Bay enclave of homes that includes neighborhood tennis courts and private beach access. Just a short walk to the beautiful Gulf of Mexico and beach. Great open floor plan perfect for entertaining and enjoying the Florida lifestyle. Very private and spacious master suite with views of the pool and canal. Attached poolside cabana style fourth bedroom suite that is pool side with separate entry. Outdoor space is complete with gas grill, swimming pool with solar cover and a boat dock with a lift. Two car garage. Pet Friendly.
1945 Gulf of Mexico Dr. #307
Area: Longboat Key
GREAT Longboat Key location. This 2 bedroom, 2 bath condo has been totally updated. A southern exposure offers a partial view of the Gulf of Mexico from the screened balcony. HD flat screen TVs, wireless internet. Seaplace offers 2 swimming pools, Har-Tru tennis courts and a fitness center. A very short distant to St. Armands Circle & downtown Sarasota, for shopping, great restaurants and the theatre. Available for a seasonal rental. LUXURY, GULF OF MEXICO SARASOTA VACATION RENTAL.
500 S. Washington Drive #16A
Area: Lido Key / St. Armands Key
Cute and convenient 1 Bedroom 1 Bath First Floor condo in Kingston Arms just 1 block to Lido Beach and 1/2 block to the shopping, dining and night life at St. Armand's Circle! Newly remodeled kitchen and bath with stainless appliances and shower in master bath. Heated community pool and hot tub just steps away from this great location. Community laundry. Assigned carport parking. Sorry, no pets allowed.
597 Yawl Lane
Area: Longboat Key
If you like to be on the water this newly upgraded Country Club Shores home has outstanding views of Sarasota Bay. Be the first to experience this comfortable open-concept home, one in from the bay, with fabulous water views that begin as soon as you step in the front door. It’s newly furnished and decorator designed from top to bottom, complete with 4 flat screen TV’s; three full updated baths; hard wood floor and vaulted 10 foot ceiling in living area; circular drive two car garage; boat dock; heated pool and spa; walk to gulf beach on deeded right of way. The understated exterior belies what is found inside. This home is located at the southern end of Longboat Key with very close proximity to St Armands Circle shops and restaurants. 
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!
2425 Gulf of Mexico Drive, #4E
Area: Longboat Key
LONGBOAT KEY, this two bedroom, two bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award-winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen. A five minute walk to shopping & pharmacy. Short drive to St. Armands Circle or downtown Sarasota, for restaurants & theaters. SARASOTA FL, BEACHFRONT, GULF OF MEXICO, LUXURY, SEASONAL RENTAL.
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.
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.

Showing Results 1 - 15 of 94