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 29
101 Sunset Drive #402
Area: Downtown Sarasota
Spacious and well appointed condo in gated and secure Lawrence Pointe with fabulous views of the Sarasota Bay! Walk to the Van Wezel and everything downtown has to offer. This two bedroom/two bath unit with large office in one of Sarasota's nicest and well maintained Bayfront buildings has it all. There are wonderful water views, a lovely custom kitchen and plenty of customized closet space. This is a serene and relaxing space with plenty of room to unwind. The large master suite offers a balcony with lovely green city views by day and sparkling lighted views of Sarasota by night. The large office offers built in shelving and large custom closet. There is also a large laundry room in the unit with a high end washer and dryer and plenty of storage space. Enjoy swimming in the pool alongside the bay and take in the beautiful views and wildlife up close. You will love living the Sarasota lifestyle in this beautiful condo right in the heart of downtown so close to dining, shopping, the opera and all the arts and cultural activities that our city is known for. Owner is offering the unit as a furnished annual rental but would consider a seasonal rental of at least 5 months. Sorry, no pets
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.
1740 Alderman Street #9
Area: Sarasota
Beautiful two bedroom/two bath townhouse tucked in a quiet section of downtown Sarasota just off of Burns Court. This tranquil setting provides a relaxing oasis so close to the theatre, dining, shopping, the bay front marina and everything else that downtown Sarasota has to offer. There are water views from the living area as well as the master bedroom. Your deck overlooking the bayou is a perfect spot to enjoy brunch or an evening glass of wine. Walk to everything and be part of the vibrant downtown scene. Also convenient to Lido Beach and St. Armand's Circle, this condo has it all. The community pool is large and includes a grill area overlooking the bayou. Under building reserved parking space goes with the rental.
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.
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!
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.
1350 Main Street #1005
Area: Downtown Sarasota
DOWNTOWN SARASOTA** 1350 MAIN**LOCATION is the Best!! This TURNKEY FURNISHED OPEN FOR SEASON 2018 THREE MONTH MINIMUM STAY- 1 bedroom, 1.5 bath condo is on the 10th floor of 1350 Main Street building. Upgraded and lovingly cared for. The living room opens onto the terrace and enjoys a peaceful views. Master Suite has large walk-in closet, a spacious master bathroom with separate tub and shower and double sinks. The kitchen is well appointed and there is a laundry room and half bath for guests. This unit has one parking space in the secure garage. 1350 Main, built in 2007, has an on-site manager and 24 hour concierge service, community pool, fitness center. Enjoy Sarasota in this downtown condominium. Steps to restaurants, shops, theaters, bookstore, art galleries and the weekly farmer’s market. 15 minutes to our wonderful beaches.
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. 
808 3rd Avenue West #104
Area: Downtown Bradenton
A luxurious high rise in the heart of Downtown Bradenton along the Manatee River , The Promenade at River Dance offers the ultimate in resort living located in the heart of downtown . Enjoy the community social room, heated pool, theatre room, state of the art fitness room, rooftop lighted tennis, putting green and basketball court. This ground floor unit is turnkey furnished and tastefully decorated with all the comforts of home. Some of the features include ,ceramic tile, granite counters, stainless steel appliances, W/D and a large garden tub. Enjoy a sunset from your private lanai or stroll the Riverwalk to the marina, shopping, restaurants & theatre, River Dance offers something for everyone!  2 months minimum for high season.   NO Pets. 
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
7710 Lake Vista Ct. #306
Area: Lakewood Ranch
LAKE VISTA RESIDENCES @ LAKEWOOD RANCH. Like new beautifully appointed 2BD/2BA 1,763 SF, 3rd Floor TURNKEY FURNISHED. Very spacious interior and a private screened balcony terrace to relax with the views of the preserve scenery. Enjoy the Lakewood Ranch lifestyle at this beautiful condominium and community that features: grand clubhouse, fitness center, resort style heated pool and spa & gas barbecue. Walk to Lakewood Ranch Downtown shopping, dining, cinema and activities. Minutes to the new UTC mall.
235 Cocoanut Avenue #121D
Area: Sarasota
Downtown living at its best! You will love this gorgeous modern townhouse in the heart of downtown. The home has four amazing stories with a private elevator and two car garage. Enter inside the light-filled foyer and private office. Second floors totally open with a large kitchen, dining, and living area. The kitchens and bar are adorned with exotic countertops. Fine cabinetry, lighting and stainless steel appliances are part of the appeal of this modern urban living condo. The third floor consists of a master suite with an on-suite bathroom as well as a guest bedroom. The master is full of light with unique draperies and a custom walk-in closet. The fourth floor is up in the sky, totally open and spectacular bar busted with natural light. A wall of sliding glass doors open to a terrace, with a side view of Sarasota Bay.
1350 Main St. #1202
Area: Downtown Sarasota
Sensational Sarasota Bay Views from this 12th floor two bedroom turn key furnished condominium. Perfectly located in downtown Sarasota in walking distance to the waterfront, restaurants, shops, galleries, theaters, and Whole Foods. Master bedroom features a king size bed and the second bedroom has a sleeper sofa queen size bed. Wood floors in the main living area and many upgrades throughout. Secured parking and 24 hour concierge service. Available for a three month or longer reservation.
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.
1111 Ritz Carlton Drive #1107
Area: The 'Ritz-Carlton'
RITZ-CARLTON in downtown SARASOTA. The ultimate in LUXURY living. Enjoy all of the amenities this property has to offer which includes the GOLD MEMBERSHIP available to you. This two bedroom, two & a half bath condo has a large foyer, large living room with a balcony overlooking the pool & sunsets. Cooks kitchen with upscale appliances, granite counter tops & a built in wet bar. Fabulous views of the cityscape, sunrises & sunsets. The spacious master suite has a spa tub, walk in shower and a balcony overlooking the city. The split floor plan allows privacy for you and your guests. Walk to downtown restaurants, shopping, theatres and art galleries. LUXURY, SARASOTA, DOWNTOWN, WATER VIEWS.

Showing Results 1 - 15 of 29
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