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 31
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 #1006
Area: Downtown Sarasota

Gorgeous sleek, high end decorated, turnkey furnished condo in the beautiful Alinari building.  City views abound as you look eastward and see the sunrise each day.  The condo has two bedrooms, two bathrooms, comfortable living room/dining room/kitchen combination.  Split floor plan.  Master bathroom has double sinks and a tub and separate stall shower.  Guest bathroom has a single sink and shower.  Master bedroom has a king sized bed and Sarasota city views.  Guest bedroom has two twin beds and views of the sparkling lights of the city.  Alinari amenities include:  concierge, fitness center, pool with spa, BBQ grills, movie theater, meeting rooms and business office.  Assigned parking.  No pets allowed due to Association rules.  Available immediately for an annual rental.

1350 Main Street #1503
Area: Downtown Sarasota
DOWNTOWN SARASOTA...the best and most desirable location in downtown. 2 bedroom, 2 bath, split floor plan with a stunning view of the City. If urban living is your style this is the place for you. State of the art kitchen appliances. exquisite furnishings, top of the line linens. Two assigned parking spaces in a secured parking garage. Great amenities, heated pool and spa, library/sitting room, extensive fitness facilities, meeting/business/gathering rooms. Walk to shopping, fine and casual dining, the beautiful Sarasota Bayfront. SARASOTA VACATION RENTALS, LUXURY, GULF OF MEXICO.
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. 
1350 Main Street #808
Area: Downtown Sarasota
DOWNTOWN SARASOTA...the ultimate of Urban/Metropolitan living. Experience the attractions of theaters, opera performances, art galleries & events, wonderful restaurants to choose from, shop the boutiques. This two bedroom, two bath condo has all new furnishings, tray ceilings, crown molding, hardwood floors. Fully equipped kitchen with granite counters, wood cabinets and stainless steel appliances. Enjoy all of the amenities, secure garage parking, 24 concierge service, heated pool and spa, state of the art fitness room, club room for entertaining. Walk to the Sarasota Bayfront for magnificent sunsets. Enjoy the convenience of Whole Foods grocery store only a few blocks away. This unit is available for a short term rental from June 1 to September 30. LUXURY, SARASOTA, VACATION RENTAL.
50 Central Ave. #1604
Area: Downtown Sarasota
Exceptional downtown Sarasota living at 50 Central! Walk to restaurants, shops, galleries and more! Enjoy spectacular Sarasota Bay views from this large 2 Bedroom/2 Bath luxury condo. Relax watching sunsets from your private balcony. Stunning unit features 72" plasma TV in living room, tile floors, wood cabinets w/granite counter tops, stainless steel appliances, in unit washer/dryer. Lots of closet space for added storage. Pool, spa & fitness center. One garage parking space. Can be rented Seasonal with one month minimum, or longer term. Enjoy Suncoast living.
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
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.
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.
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!
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.
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 #303
Area: Downtown Sarasota
2 Bedroom, 2 bath furnished unit in the Alinari. Close to downtown, walk to the arts. Full Bay Views. Amenties include pool,spa, fitness center, billiards and club room, theater, security. Walk to all that downtown has to offer in terms of shopping, dining and cultural venues.
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.
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!

Showing Results 1 - 15 of 31
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