Southwest Florida Vacation Rentals

Jennette Properties has luxury vacation rental properties throughout Sarasota and Manatee County. Our properties are spacious and modern to provide you with the best stay possible. Our properties are close to nearby attractions, dining, and entertainment options.
If you're looking for the best vacation rentals in Sarasota or surrounding communities, check our inventory of properties available.

Showing Results 1 - 15 of 64
1843 Burgos Drive
Area: South Sarasota
Spacious 3 bedroom, 2.5 bath at a GREAT price. Divosta built reinforced steel and solid concrete construction. Brick paver drive, seamless gutters, galvanized steel hurricane shutters, automated sprinkler system and privacy wall. Tile throughout, 4 lighted tennis courts, bocce ball and basketball courts, tot lot, lakeside gazebo, service kitchen, resort living at an affordable price. Tastefully decorated, turnkey furnished, all new furnishings, 3 queen beds, close to shopping, 10 minutes to Siesta Beach. Great outdoor living area. Available for season.
3781 59th Avenue W.
Area: IMG Academy Area
This ground floor 2BR/2/BA condo with fire place is located next to IMG Academy, less than 12 miles from Anna Maria Island and Holmes Beach and only 12 miles from the region's newest world-class fashion and dining destination - the Mall at University Town Center (UTC). Mirror Lake Condominium's amenities include a community pool, spa, sauna, tennis courts, playground, pickle ball, and bocce ball. The unit has it's own washer/dryer. Three month minimum. Long term available as well. No Pets.
6281 Timberlake Drive H-6
Area: Sarasota
This beautiful light, bright, tastefully decorated Villa boasts vaulted ceilings, ceiling fans throughout, and a gorgeous screened in lanai with serene views of the golf course. The extended master bath includes a lighted vanity. Location! Location! Location! This villa is located just minutes from our beautiful gulf Beaches, University Town Center Mall and I75.
11625 Garessio Lane
Area: South Sarasota
Beautifully furnished 2 bedroom 2 bath villa with private heated pool in The Isles of Sarasota in Palmer Ranch! Queen Bed in both Bedrooms, 2 car Garage, nice size Laundry Room. The Isles offers a heated lagoon style pool, fitness center, tennis courts, bocce ball court, basketball court, tot lot and clubhouse with a post office and full time activities director. Minutes away from Siesta Key Beach, Legacy Trail and lots of shopping and dining close by. Sorry no pets allowed. Available as a seasonal rental only.
4111 25th St. W.
Area: IMG Academy Area
Location Location! This quaint 2 bedroom 2 bath home is in the center of it all. The house has been recently updated and has new furnishings throughout. Open floor plan allows everyone to stay connected as food is being prepared and everyone is winding down from the days activities. Master bedroom features a queen size bed, soothing décor and a flat screen TV for those late night shows. Guest bedroom features two twin beds, some fun décor, highlighted with a pop of orange. As you walk past the kitchen, through the French doors, you can stop in the dining area for your morning coffee and peer out into the spacious backyard oasis. The backyard features a floating deck with covered gazebo. There is a fire pit for those evenings you just want to relax outside. A BBQ grill is available for your dining pleasure. The home is centrally located in Bradenton. Just a few miles to the beach, close to shopping, dining, the Red Barn flea market and downtown Bradenton. Take some time to visit The Ringling Museum and the Dali Museum in the neighboring cities. If you like to shop, the Ellenton Outlet mall and the Mall at University Town Square will take good care of you. Don't forget, Busch Gardens, Disney, Universal Orlando and Sea World are just a few hours away. The Garage is NOT available for tenant use. Available High Season (Jan- April), Off Season (May-August). September is not available. October -December available. Weekly rent is available. Sorry No Pets & No Smoking.
8397 38th St. Cir. E.
Area: Sarasota
Beautiful second floor 2 bedroom Condo in the gated "resort-like " complex of Serenata . Pool, tennis and fitness are on the premises. This unit is updated and very nicely Turnkey decorated. 2 Queen beds and separate full baths allow for 2 couples or guest privacy. Flat screen T.V's in Living room and Master bedroom. Pets are welcome within the community guidelines. Very convenient to many shops and restaurants. Seasonal rentals include all utilities with an Electric cap of $75.00
4210 Breezeway Blvd. #425
Area: Sarasota
Turnkey furnished 3 bedroom 2 bath Townhome. Located in gated community of Pinestone at Palmer Ranch. Tastefully decorated with the 1 bedroom with King size bed on the 1st floor. The guest bath along with the 3rd bedroom which is set up as an office/den area are also on the main floor. The Master suite with a large en-suite bath is located upstairs for privacy and has a king-size bed and TV . The screened-in lanai overlooks a private wooded area and has an electric grill for your outdoor cooking. Pinestone offers many amenities such as a clubhouse with theater ,heated pool, hot tub and fitness center,2 tennis courts and basketball courts. Located near shopping, parks, The Legacy bike trail, Stoneybrook Golf and Country Club which is open to the public and our famous Siesta Beach!. Everything you need for the perfect vacation rental. This community does require a 90 day minimum and a small pet is welcome! Call for off-season rates
4560 Bliss Road
Area: Sarasota
Charming 1bdrm./1bath, 1st. floor attached apt. in a private tropical setting,(only one other dwelling on the property) immaculate, recently renovated, kitchen has all new appliances, room for your boat or RV, large attached private lanai with outside grill, location is about 15 min. drive to Siesta Key Beach and Village, close to shopping and restaurants. This special place is available for 2016 season, 30 day minimum required.. No pets or smoking please. Please contact us for any additional information needed.
851 Tartan Drive #11
Area: Venice
This freshly painted 2 bedroom 2 bath villa with open floor plan with cathedral ceilings and generously sized rooms. The Florida room is perfect for drinking your morning coffee or tea while looking out at the relaxing lake views. Also, a nice patio to further enjoy time outdoors. A short stroll to the clubhouse and heated community pool for additional entertainment. All within 15 minutes of the downtown historic district of Venice, Gulf beaches, shopping, dining and more! This property is open for season 2017
1515 Pelican Point Road #285
Area: Sarasota
This 2nd floor unit is light and bright with warm tropical colors and light furniture, tile and hardwood floors throughout, updated furniture and accessories, eat-in kitchen and formal dining room. The view is of Little Sarasota Bay overlooking Siesta Key and the entrance to the Yacht Harbor at Pelican Cove. The washer and dryer are enclosed in the glassed-in porch along with a sitting area with comfortable Futon for extra visitors. 
1534 Ernesto Drive
Area: South Sarasota
Beautifully furnished spacious town home with lake views. Large open plan kitchen for the resident chef. One bedroom downstairs and two upstairs. Lovely lake view from upstairs balcony. Community offers exceptional sports and social activities for your visit. Close to shopping,restaurants, and beaches. Owner will permit one small dog only. HOA requires a 4-month minimum stay. Check "The Isles" website for all the community activities.
6612 Schooner Bay Circle
Area: Sarasota
Schooner Bay is just south of the Siesta Key Stickney Point Bridge. This is  turn key furnished two bedroom end unit with a one car attached garage and a 24' boat dock. Very private setting with scenic foliage views. Steps to the pool. Tile throughout. The 24 FT deeded boat dock slip with electric has direct access to the Intercoastal Waterway. Walk along the canal or take your boat to Sarasota Bay-no bridges to Bay. Walk, bike, or drive to the Siesta Key Beaches less than one mile away. Seasonal rates and short term monthly stays are available.
7061 Hawks Harbor Circle
Area: Bayshore Gardens
HAWKS HARBOR ESTATES...this magnificent 3 story home has 4 bedrooms, 4.5 bathrooms and an elevator. The gourmet kitchen is sure to please any cook with granite counters, solid wood custom cabinets and a breakfast bar. A great room overlooking the lake, pool and spa. All of the bedrooms are en suite which allows for plenty of privacy for your guests. On the third level there is a lovely sitting room, bedroom and full bath. Outside by the caged pool and spa there's an enormous area for entertaining. Large three car garage. Enjoy watching beautiful sunsets on SARASOTA BAY. Convenient to shopping, SARASOTA AIRPORT and a short drive to DOWNTOWN SARASOTA. In door out door surround sound. Private boat dock with a lift, just minutes to the open waters of Sarasota Bay and our beautiful beaches on the GULF OF MEXICO. Once you've entered the gates of this community you will feel like you've found paradise in this tropical setting.
4655 Tower Hill Lane #2424
Area: South Sarasota
Bright open floor plan, 2 bedroom 2 bath condo plus den on second floor. Screened lanai with preserve view, one covered parking space, close to heated pool and tennis courts, social membership available if desired for $125. Stoneybrook is a gated community with state-of-the art clubhouse offering fine and casual dining, fitness center, several heated pools, lighted har-tru newly renovated tennis courts. Close to shops, restaurants and beautiful Siesta Key beach.
3119 Live Oak Lane
Area: Palmetto
This end unit villa located in the gated community of Terra Ceia Bay Club, is ready for winter guests. This 2 bedrooms with a den, which is set up as an office, 2 baths has an open floor plan and a nice size kitchen with a sliding glass door that leads to the enclosed lanai. The master bedroom has a king size bed and the guest bedroom has a full size trundle bed with a twin bed for little ones or over nite guest. The office has fax machine for those working on vacation. This community is pet friendly and you are a short distance to the community fishing pier, boardwalk and on site dinning The Sunset Grill. Community pool, tennis and golf course can be purchased for a small fee. This community is perfect for those who like power walk or for a evening stroll. Full size washer and dryer on premises. Easy access to I-75, 275, Ellenton Prime Outlets, dinning, library, dinning, Sarasota, St, Peter, Tampa. Owner will accept a small pet with a non-refundable pet fee.

Showing Results 1 - 15 of 64