Siesta Key Vacation Rentals

We have vacation rentals along Siesta Key with sunny beaches on the gorgeous Gulf of Mexico with picturesque sunsets and world renowned crystal-white, powdery sand that stretch for miles. Siesta Key is a barrier island off of the central western coast of Florida . It is situated between Sarasota Bay and the Gulf of Mexico. There are shops from the chic and elegant to the hip and funky, with all sorts of fashion, beach accessories and souvenirs. Siesta Key offers restaurants where you can go to grab a quick breakfast or lunch in your flip-flops or to relax in style over an extraordinary dinner. The Siesta Key vacation rentals here are luxurious. The Siesta Key Beach is voted #1 Beach year after year!


Tour Siesta Harbor on Siesta Key

Showing Results 1 - 15 of 32
1640 Summerhouse Lane #10
Area: Siesta Key
Arrive in style with your own private elevator into your foyer. This spacious condo is light and bright with a southern exposure. Entertaining and relaxation is at its finest with a huge bricked terrace serving a table for eight plus 2 lounges. Beautiful glass dining table. All upscale appointments in a contemporary bldg ready for you to explore world famous Siesta Key. Master bedroom has king sized bed, LR has HS internet, DVD. & leather sectional. Kitchen has stainless, granite and open bar with stools. Like new condition.
1250 N. Portofino Drive #301
Area: Siesta Key
Siesta Harbor is a 55+ community overlooking Sarasota's Intracoastal Waterway. This south-facing end unit features two bedrooms and 2 baths with a King in the Master and twins in the guest bedroom. The community laundry room/storage room is next to the elevator. Cable, phone and Internet are included with the rental. Boat slips right outside your door are available for a nominal fee. Deeded beach access across the street. The community offers social events and card games for winter guests with full use of the clubhouse, sauna, fitness, heated pool & spa and shuffleboard court. Take a short walk to the south village for shopping and dining or hop on Jonny's free rides for a short trip to the public beach or Siesta Key Village for more entertainment and fun. Relax on your lanai with your morning coffee and watch the boats go in and out of the Harbor. No pets allowed.
1257 S. Portofino Drive #107
Area: Siesta Key
This 55+ community is ideal for your winter vacation. Enjoy your morning coffee from the lanai over looking the intercostal. Amenities include direct beach access to Siesta Key beach, the #1 beach in the USA, community pool and spa, sauna, fitness, shuffleboard and walking distance to shops, restaurants and entertainment. Close proximity to the Stickney Point bridge enables easy access on and off the Key. 
5911 Midnight Pass Road #103
Area: Siesta Key

Stunning 2bdrm./2 bath condo situated on Siesta Key, steps to the beach this newly renovated condo has views of the dock and bay, private boat slip will accommodate up to a 50' boat, gourmet kitchen with new appliances and designer furnishings. No pets allowed. Available off-season, call for High Season Prices 

231 Garden Lane
Area: Siesta Key
Wow!!:::Spanish Mediterranean beauty available for season. Almost 4300 sq.ft. open plan, high ceilings with 4 bedrooms, 5 baths, neutral tile, granite counters, hardwood cabinets and floors, double stairway, huge media room and outdoor deecks overlooking tiled pool & spa. 2 bedrooms, + 3 baths, and office downstairs. Master retreat and media room and 2 full baths upstairs. Gorgeous home available long or short term.
1300 North Portofino Drive #S208
Area: Siesta Key
Turnkey furnished annual rental on Siesta Key at Siesta Harbor, a 55+ community. This 2nd floor corner unit has beautiful views of the harbor and the Intracoastal Waterway. Boat slips available to renters. 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. Move right in to this turnkey furnished 2 bedroom unit with gorgeous harbor views. Laundry room is on the same floor.
5238 Winding Way
Area: Siesta Key
Fabulous home in Siesta Key minutes away from the famous Siesta Key beach and the Village of Siesta Key. Gorgeous house with very private settings, features 3 bedrooms, 3 bathrooms, huge chef kitchen, open lanais on second floor with beautiful views of the preserve. Ground floor with enclosed lanai, car garage, storage for bikes, kayak and much more. Second floor boasts an open plan, bright and tranquil settings with amazing kitchen, open lanais and laundry room and 3rd bedroom. 3rd floor with guest bedroom and private bath, master suite with its own suite bathroom with double sinks, separate shower, tub, walk-in closet. Home is surrounded by lush tropical landscaping. Ride the bikes to Siesta Key beach, and explore what this amazing Island have to offer. Excellent location, private street, conveniently located close to the beach, Siesta Key village, downtown Sarasota, entertainment, shopping, golf and so much more. This is your absolute best vacation spot! Vacation rentals, Siesta Key, Sarasota, seasonal. Dogs OK. Welcome to Paradise!!! Once you are here.. you won't want to leave
1257 S. Portofino Drive #104
Area: Siesta Key
Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. An open kitchen and remodeled bathrooms are some of the perks in this waterfront unit. Sit on your lanai and watch the boats go by as you sip your morning coffee. Amenities include direct beach access to Siesta Key beach, the #1 beach in the USA, community pool and spa, sauna, fitness, shuffleboard and walking distance to shops, restaurants and entertainment. Close proximity to the Stickney Point bridge enables easy access on and off the Key. This is a 55+ community which means one renter in the party must be over 55 years of age. No pets and no smoking please. 
1104 Point of Rocks Road
Area: Siesta Key
Charming 2nd floor, 2bdrm/1bath immaculate beach cottage, located 1 block from Siesta Key Beach, incl. washer and dryer and under building parking. Available April 1, 2015 for summer rental (call for price) or seasonal. Small pet may be allowed with owner approval.
1257 Tree Bay Lane
Area: Siesta Key
Expansive four bedroom home on the water on South Siesta Key is available for season 2017. Through the entrance on the first floor you enter into the family room with views of the pool and intracoastal waterway. There is also a bedroom and private bathroom on this level. Up the open staircase leads to the main living floor with a skylight over the open plan kitchen, dining room and living room. All of these rooms overlook the pool and the intracoastal waterway. The master bedroom also has a comfortable sitting area and also a water view, the master bathroom features a large tub and separate shower, with double sinks. All bathrooms have been recently updated, and the bed sizes in all the remaining bedrooms are queen sized. The house also has 2 sofa beds, perfect for extra guests. There is a dock at the house and the beach access is a short distance. Available for Season. SINGLE FAMILY HOME SIESTA KEY SARASOTA FLORIDA SEASONAL RENTAL
1622 Stickney Point Road #202
Area: Siesta Key
View the intracoastal from your master bedroom porch having a rest on the reclining chairs. This second floor townhouse is in the perfect location for your stay in SARASOTA and a short distance from a world famous beach. Located by the Stickney Point Bridge this renovated and beautifully decorated townhouse is ready for short term stays of a minimum of one month. Up the stairs to the front door and step into this light filled home, all up to date decorating in neutral tones. There is a guest bathroom on the first floor and an extra single bed for overflow guests. Up to the bedroom level and you will find two bedrooms, the master has a king sized bed and the second bedroom features a queen sized bed. There are two porches for relaxing on, one off the living room and one off the master bedroom. There is a washer and dryer in the unit, and the resort style complex features two swimming pools, one overlooking the bay and tennis courts. SARASOTA, NEAR SIESTA KEY, RENTAL.
9393 Midnight Pass Road #502
Area: Siesta Key
Enjoy this bright 2 bedroom 2 bath condo on the 5th floor. You can sit on your lanai and enjoying your morning coffee and in the evening and watch the wildlife. The kitchen is updated and it allows for the open view of the intercostal water way. Both bedrooms have king size beds. This is the place to stay if you like quite neighborhoods. Open for December 2016, January 2017 and February 2017
1257 S. Portofino Drive #205
Area: Siesta Key
Your winter vacation getaway! Come join the fun at Siesta Harbor this winter. An active 55+ community on the Intracoastal Waterway with Harbor and Bay views from every unit. Social events at the clubhouse include cocktail hours, potlucks, bridge, poker, book club, movie night and more. This second floor unit is conveniently located near the elevator and community laundry room. Beautifully updated with a King bed and a queen sleeper sofa. Relax on your lanai and watch the boats come in and out of the Harbor. Direct beach access across the street to the #1 beach in the USA, Siesta Key Beach. Amenities include heated pool and spa, fitness room, and shuffleboard. Fishing Pier on the Intracoastal and boat slips available.
9008 Midnight Pass Road #4
Area: Siesta Key
Units in The Sea Breeze boutique condominium are rarely available for lease and provide an opportunity to vacation in peaceful luxury. Located on the quiet southern end of Siesta Key, the home provides gorgeous views of a nature preserve, Blind Pass and the Gulf of Mexico, a short walk takes you to the recently expanded Turtle Beach and a short drive takes you to world famous Siesta Beach and Siesta Key Village. But you may not want to leave the beautifully furnished 3800 sq. ft. home that occupies the entire 4th floor of the building with direct elevator access and a fully equipped gourmet kitchen. Enjoy amazing sunsets on the large tile balcony that spans the length of the building. The heated community pool and spa are available to only 5 residences. Guests have full use of the 2 car garage and boat dock. ONLY AVAILABLE DECEMBER, JANUARY AND FEBRUARY OF THE 2017 SEASON- JANUARY OR FEBRUARY RESERVATION MAY BE CONSIDERED. SORRY, NO PETS AND NO SMOKING.
4632 Ocean Blvd.
Area: Siesta Key
Island Lifestyle right on the Gulf on Mexico in this gorgeous estate available for longer term rentals. Loads of charm and history in this house situated down a long private driveway off Ocean Boulevard. The house has been lovingly restored. Walk into this house and immediately the charm of the home is evident. There is a separate living and dining areas each with their own fireplace, an eat in kitchen plus an additional family room. The master suite is on the ground floor, and from the bed it is possible to look across the Gulf of Mexico with unobstructed views. All three bedrooms upstairs are en-suite. The main house is next to the water with two stories and some of the bedrooms are upstairs. There is a recreation room/apartment with a separate kitchen and bathroom on the opposite side of the pool in the unique cabana. Perfect as the pool cabana, rec room or just extra space from the main house. The pool is private with a raised breezeway along the side and perfect for exercising and play. Behind the cabana is the covered parking space. On the property there is a sea wall and a fishing pier. This home is located on the north end of Siesta Key just a short distance from the world renowned Siesta Kay beach with shopping and restaurants of the Siesta Key Village. SINGLE FAMILY HOME, SIESTA KEY ON THE GULF OF MEXICO!!

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