Southwest Florida Urban Vacation Rentals

Jennette Properties has luxury vacation rentals throughout the heart of Sarasota and the Gulf coast. Our properties in Downtown Sarasota offers luxury and spacious living while close to all the shops and attractions that Sarasota has to offer. Nice condo units and single family homes available.
If you're looking for the best vacation rentals in Downtown Sarasota with all the amenities and attractions you can get, check our inventory of properties available.

Showing Results 1 - 15 of 32
750 N. Tamiami Trail #604
Area: Downtown Sarasota
Gorgeous , very well maintained condo in sought after downtown Sarasota. This beautiful Renaissance unit boast wood floors throughout the main living area and high end luxurious carpeting in both bedrooms. The master has a king size bed and large screen TV. Secondary bedroom has two twins. There is a washer dryer in the unit. The building is two blocks to the heart of downtown. Enjoy relaxing in the community pool or getting in your workout in the state of the art fitness center. The Van Wezel is just across the street with amazing Broadway shows. This is your perfect winter get away!
464 Golden Gate Point PH 9C
Area: Downtown Sarasota
Luxury Living on the Bay in downtown Sarasota. One of the most beautiful penthouse residences imaginable with views in every direction. Over 6,000 square feet of opulent luxury. Enter from the private elevator into the entryway with a lighted starred domed ceiling. Impeccably decorated with the finest of furnishings, dining room, home theatre, game lounge and huge gourmet kitchen. Formal living room has coffered ceilings and features a bar that was inspired by the Ritz hotel in London, complete with lighted stained glass panels. Walk in temperature controlled wine cellar. His and hers bathrooms, beautifully decorated with marble and also two separate offices with fine wood paneling. Split bedroom plan, featuring fine linens and luxurious bedding. Four terraces with views in every direction including the Sarasota marina, downtown and the Ringling bridge from the west terraces. Boat dock, pool, exercise facilities are amenities to be enjoyed in La Bellasara. This condo is available for season 2018.
11 Sunset Drive #104
Area: Sarasota
Sarasota vacation rental. This is a wonderful long term or seasonal lease. This light, bright unit has been maintained beautifully, newer carpet, tastefully decorated, stainless steel appliances, views from every room. One small well trained dog allowed. This is your perfect seasonal get-away!
1111 Gulfstream Avenue 16E
Area: Downtown Sarasota
Ideal location on the downtown waterfront. Two bedroom, two bath condo with upgraded kitchen and bathrooms with granite counters and solid wood cabinets. A 10 X 10 bonus room. Gorgeous views from every room. Stunning new floor to ceiling impact resistance windows in every room. Large, oversized balcony with all new stainless steel railings and shatter proof glass. Combination washer and dryer in the unit. Reserved parking in the garage. Two tennis courts and a new salt-water heated pool, new grills and new landscaping. Very tastefully decorated. ONE WATERGATE is ideally located with easy access to downtown Sarasota, restaurants, theaters, shopping, the Ritz Carlton, St. Armands Circle and Lido Beach. Call now for a showing, this property will not last.
5531 Key West Place
Area: East Bradenton
Enjoy lush landscaped preserve view from this spacious first floor unit. Newly furnished two bedroom two bath condo in gated community within minutes of I-75  is ready for immediate occupancy. Harborage amenities include heated pool and spa, boat dockage, riverfront park, nature trails and much, much more.
3756 82nd Avenue E. Circle #104
Area: Sarasota
Resort style living. Minutes away from downtown Sarasota, the beaches and airport. This corner unit has 3 bedrooms, 2 and half baths and 1 car garage. The lanai overlooks a beautiful lake. This end unit is arguably the best location the development. This townhouse features custom painting, corian counter tops, wood cabinets, GE appliances, including washer and dryer. Ceramic tiles in kitchen, living and dining areas, with wrought iron railing for the staircase. Decorative moldings on walls and ceiling. Master bedroom with King sized bed and in suite bath is on first level. Two additional bedrooms. Carpet in all bedrooms. This beautiful landscaped community has curb appeal with the garages and driveways to them at the rear of the town houses. Community also includes Pool, Play Grounds, Tennis/Basket Ball courts, Grill area and Gazebo. 
750 N. Tamiami Trail #916
Area: Downtown Sarasota
Gorgeous upscale CONDO in DOWNTOWN SARASOTA available for short or longer term stays, three month minimum. Wood floors and carpet in the bedrooms, updated and designer furnishings for the guests. Comfortable living room furnishings, all coordinated perfectly with wood floors. High views looking east over Sarasota and the surrounding area, perfect to see the sunrise from the balcony. Enjoy all that the Renaissance has to offer, first class gym, pool and hot tub, meetings rooms, private exercise facility, massage rooms, entertaining spaces and a barbeque poolside for use. 24 hour security in this gorgeous building situated in the Sarasota Arts District, just a short distance from downtown and all that it has to offer.
800 N. Tamiami Trail #307
Area: Downtown Sarasota
SARASOTA THEATRE DISTRICT...large 2 bedroom plus a den with a queen size pull out sofa & two bathrooms. This unit is located in the Alinari building, two blocks away from downtown Sarasota. Heated community pool & spa, outdoor grills by the pool, fitness center, theatre room, business center and a community room. A secure building with 24 hour concierge. A short drive to St. Armand's Circle, Lido beach, shopping, theaters and many wonderful restaurants to choose from. An assigned parking spot and plenty of guest parking. Call now to secure this property for Season or off Season. LUXURY, SARASOTA, DOWNTOWN, BAY FRONT.
301 S. Gulfstream Avenue #102
Area: Downtown Sarasota
DOWNTOWN SARASOTA SEASONAL IN St. REGIS. This building is located on the corner of Ringling and Palm Avenue with frontage on South Gulfstream, across the street from the Sarasota Bay! Perfect location with easy access to all that downtown Sarasota has to offer. Completely re-modeled two bedroom, two bathroom condo with updated kitchen and beautiful bathrooms. All brand new upscale furnishings and decorating . Beautiful wood floors and plantation shutters on all windows.
800 N. Tamiami Trail #203
Area: Downtown Sarasota
Gorgeous contemporary two bedroom, two bathroom with western exposure available in the luxurious Alinari building in downtown Sarasota, Florida. Across the road from the Arts District and the Van Wezel, Symphony, etc. Walking distance to grocery store, theatres, bus stop and restaurants. Available immediately for long term tenant. Light and fresh decorating with tree top view west. Enjoy all the Alinari has to offer with their world class swimming pool and hot tub area/recreation area plus gym and community rooms and theatre. SARASOTA, ANNUAL FURNISHED CONDO
800 N. Tamiami Trail #1006
Area: Downtown Sarasota
Gorgeous sleek high end decorating in this city view condo in the beautiful Alinari. Views high above the city looking eastwards and the sunrise. Just a block away from a shopping plaza with a grocery store, all sidewalks and bus routes nearby. Two bedrooms, two bathrooms in this spacious condo, designer furnishings and completely available immediately! Long or short term of three months or longer are available in this building. The Alinari features luxury amenities which include a large gym, pool and spa, game room, movie theatre etc.
800 N. Tamiami Trail #1010
Area: Downtown Sarasota
DOWNTOWN ALINARI TURNKEY FURNISHED. RESORT style living at the ALANARI. Newly Furnished and freshly painted and new carpet. Sunny open floor plan with large master suite with a king size bed and 40" Flat screen TV, large walk in closet and master bathroom with garden tub and walk in shower. Living room/ dining room features a 50" flat screen TV and a private terrace that overlooks the beautiful Community Pool and expansive city scape vistas. Perfect kitchen with breakfast hi-bar, granite countertops. Bedroom two features a queen size bed. Spacious laundry room. One car garage in secure parking garage and plenty of guest parking. Located on the 10th floor in the south tower within close proximity to the elevator. The Alinari provides every amenity you could need: a 24 hour concierge and security, meeting rooms, library, world class fitness center, heated pool with spa and waterfalls, wine room, media room, in-house movie theatre, billiards, Zen garden and outdoor grilling area. Walk to downtown and enjoy the restaurants, theater, opera, shopping and more. Walk along the water way and enjoy Sarasota's sunsets. Cross the bridge to St Armands Circle for shopping, restaurants, and the beach. Three month minimum stay. 
100 Central Avenue #409
Area: Downtown Sarasota
LOCATION, LOCATION, LOCATION...Beautifully appointed condo available SEASONAL or short term. Upscale furnishings with wood floors throughout. Located in downtown Sarasota in the Whole Foods Market Center walk to restaurants, shopping, theaters, the Bayfront. Enjoy living on the Suncoast of Florida, SEASONAL, VACATION RENTAL, LUXURY, SARASOTA FL. This unit is also available for an ANNUAL RENTAL. Call now for details and a showing.
445 N. Orange Avenue #208
Area: Sarasota
Urban living at it's finest CITRUS SQUARE in the Rosemary District. This unit has 2 bedrooms, two baths and an office with a queen murphy bed and a built in wood desk area. Master bedroom has a king size bed and the second bedroom a queen size bed, both beds are equipped with remote controls to adjust the beds to your comfort level and a massage feature as well. Fully equipped kitchen with all new stainless steel appliances, wood cabinets, granite counters. Living room/dining room combo with French doors to a Juliet balcony. Whirlpool duet washer & dryer in the unit. This condo has been tastefully decorated and has everything you need. Enjoy shopping and dining right on the main level of the building or walk to Downtown Sarasota for more shopping and dining. SARASOTA VACATION, LUXURY, DOWNTOWN SARASOTA, SEASONAL RENTAL.
1717 Pelican Cove Road, GL333
Area: Sarasota
Largest of the 2BR units at Pelican Cove. Freshly painted, will be putting new carpet in bdrm.. Close to main Pavillion and Tennis Courts.

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