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 83
Name
Area
Description
3203 Casey Key Road
Area: Casey Key
Get away to the privacy of the Casey Key beach, and an unusual retreat nestled right on the sand dunes. Master suite is on the second floor with views south down the beach and direct across the Gulf of Mexico. This Master Bedroom features his and hers bathrooms. On the main living area there is a second bedroom and office with a pull out bed. Available immediately for the summer.  No pets. 
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.
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. 
1 Ben Franklin Drive #22
Area: Lido Key / St. Armands Key
Gorgeous condo in the best location on LIDO KEY next to ST. ARMANDS. Available for a THREE MONTH MINIMUM rental during season for $7,000 per month. Steps away from St. Armands Circle and across the street from the beautiful Lido Key beach. Stunning views from this condo on the second floor, open beach views and wide porch accessible from both bedrooms and the living room overlooking the pool and beach. All tile floors and updated kitchen in this lovely condo. 
2901 Casey Key Road
Area: Casey Key
Welcome to Villa di Tramonto, house of sunsets, gorgeous remodeled 4 bed 4.5 bath home complete with private beach on the Gulf of Mexico. Stunning views on all levels, this magnificent home is decorated in elegant coastal furnishings. Entering the front door from the gated and beautifully foliaged entryway immediate ocean views are offered along with a sitting area, guest suite with mini kitchen, full bath and washer/dryer. Take the elevator or the inviting staircase to the spacious living areas. The custom kitchen and large dining area overlook the beach, the living room with game table and large flat screen TV and the office/den with custom cabinetry all offer stunning sunset views. The master suite and two en-suite bedrooms are on the top floor as well as a trundle/day bed on the landing for extra sleeping. The house includes marble floors, custom built in cabinetry, two wet bars, two sets of washer and dryers plus a foldout queen sofa bed on the ground floor. Relax in the living room with the windows open or on one of the two gulf -side terraces and take in the sound of the waves or watch dolphins go by. Two car garage, ample storage, an elevator, heated pool and spa complete the amenities. A private path leads to the deeded dock on the bay side for kayaking or bird watching. Casey Key destination is the ultimate spot in beach living on the West Coast of Florida, private beaches, but short distances from dining and stores. Convenient to I-75, Venice and Sarasota. 
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.
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 $15,000 a month for season which is December 1- April 30. $8,000 per month off season months May 1 through November 31. CASEY KEY, GULF TO BAY, BEACH, VENICE, SARASOTA
 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.
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.

1350 N. Portofino Drive #303
Area: Siesta Key
Siesta Harbor is surrounded by the Intracoastal Waterway with boat harbor and deeded boat slips. Boat slips can be leased for a nominal fee. This 55+ community is ideal for your winter vacation with easy access on and off Siesta Key. 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. You will love this updated 2 bedroom unit with gorgeous harbor views.
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.
1 Ben Franklin Drive #101
Area: Lido Key / St. Armands Key
FULL GULF VIEWS from this condo in the best building on Lido Key. It is situated right next to St. Armands Circle, so easy access to all it has to offer. This high rise is the ultimate in a seasonal destination. It has a three month minimum reservation. Two bedrooms, two bathrooms with all the living spaces being connected to a long balcony looking up Lido Key to Longboat Key. The view is the ultimate, from the king sized bed in the master bedroom the view is west across the beach out to the Gulf of Mexico. THREE MONTH MINIMUM, TWO BEDROOM CONDO, BEACH VIEWS, ST. ARMANDS CIRCLE, SARASOTA, FLORIDA.
131 Garfield Drive, 4C
Area: Lido Key / St. Armands Key
Lovely top floor unit in The Riviera of Lido Beach with two bedrooms two bathrooms located in the heart of Lido Key. It is a few steps from the beach, and the Lido Pavilion. Nicely furnished with all the comforts of home and this unit has a large porch that overlooks the tree tops with a view of downtown Sarasota in the distance. It is a short walk from St. Armands Circle, and a quick drive to downtown Sarasota. 
522 Bayview Drive
Area: Anna Maria Island
Magnificent Island Residence Architecturally designed and custom built with exceptional detail and workmanship throughout. Built in 2007 and situated on one of the Islands Premier Bay Front settings offering 240' of panoramic views from every room.  Outstanding Great Room design with fabulous kitchen, spacious first level owners suite, separate guest suites with adjoining family room with fireplace, wet bar and covered balcony. 28'x23' guest wing with sitting area, private bath, wet bar and covered balcony. Top of the line finishes include custom cabinetry and moldings, pickled oak flooring, tongue and groove cypress ceilings, unique lighting and custom chandeliers. Extensive decorator details including faux painting and commissioned murals. Lush tropical landscaping and lighting, infinity pool/spa with beach entry and pebble tech finish. Deep water walk around dock with vertical lift and separate 15x15 observation/fishing dock with submersed marine light. Wonderful covered porch overlooking pool and bay with outdoor kitchen and built in dining. ALREADY BOOKED for January, February, March and April 2016
2100 Ben Franklin Drive #102
Area: Lido Key / St. Armands Key
Cute one bedroom condo on the first floor of Lido Harbor South. King sized bed in the master bedroom, and fold out couch in the living room. Just steps away from the swimming pool and located right on Lido Beach. Conveniently located near the parking space, so no steps or elevators. Located a short drive from St. Armands Circle and downtown Sarasota. LIDO BEACH, SARASOTA, FLORIDA, BEACH CONDO.

Showing Results 1 - 15 of 83