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!

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Showing Results 1 - 15 of 32
Name
Area
Description
1232 Solitude Lane
Area: Siesta Key
Siesta Key luxury water front home ready for the 2016 season. NEW CONSTRUCTION. THIS 5 BEDROOM, 4 BATH FAMILY HOME ON A PRIVATE DEAD END ROAD MAKES THIS LOCATION A GREAT PLACE FOR THE FAMILY TO PLAY AND ENJOY THIS NEW HOME ON SAILBOAT WATER, WALK TO THE POWDER SANDY BEACH OF SIESTA AND VILLAGE. . THIS RELAXED LIVING HOME HAS LARGE BEDROOMS.......LARGE KITCHEN AND SEPARATE PANTRY, STORAGE CLOSET THAT CAN ALSO BE USED FOR A WINE CELLAR...CENTRAL VAC SYSTEM,CENTRAL ALARM, HEATED POOL WITH POOL BATH ...VIEWS.....BOATING IN YOUR BACKYARD....ELEVATOR...3 CAR GARAGE, OUTDOOR SHOWER NEW SEA WALL CAP, BEAUTIFUL LANDSCAPING WITH LED GROUND LIGHTING. THE MOMENT YOU ENTER THE HOME YOU WILL FEEL THE QUALITY CONSTRUCTION. A MUST SEE. THIS IS THE PERFECT WINTER GET-A-WAY!
19 Whispering Sands Dr. #805
Area: Siesta Key

Enjoy this great view of the gulf from this 2 bedroom, 2 bath condo on the 8th floor. Condo has been remodel with granite kitchen counter tops, built in cabinets in master bathroom and tile floor. You can walk out of the building directly to your own private beach. This unit is walking distance to the Siesta Key village, where you can enjoy your morning coffee and a great meal at one of the local restaurants. Sit on your lanai and enjoy a beautiful sunset.

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.
156 Siesta Drive
Area: Siesta Key
Unique FURNISHED home available for rent on Siesta Key. This single family home has four bedrooms, three bathrooms, living room, family room, kitchen with dining area, breakfast bar, two bedrooms on the second level loft, laundry room, spacious deck with two sitting areas, private pool and two car garage (ONLY one space available). The living space is on two levels with stairs to both and NO elevator. Master bedroom has a king sized bed, walk in closet, en suite bathroom with double sinks and a stall shower. Bedroom two and three have queen sized beds and bedroom four has two twin beds. First guest bathroom has a tub/shower combination and the second has a stall shower. Laundry room and third bathroom are on the garage level all other living areas on the second and third levels. Home is available for an annual or short term rental. Short term rentals must be month long or longer. Small pet allowed with the owner's approval. Available immediately.
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!!
  
5880 Midnight Pass Road #508
Area: Siesta Key
Enjoy the beautiful sunset from this 5th floor condo. This 2 bedroom 2 bath condo has been freshly painted and all new furniture. The condo is located on the Gulf side of Siesta Key. This community has private pool, tennis court and small fitness room. Walk through the beautiful court yard to your own beach. You can take a leisurely walk to the public beach as well as take the free taxi rides to Siesta Key Village for the nightly dining and music. Unit is available for season 2018.
5525 Azure Way
Area: Siesta Key
Fabulous large home decorated to perfection just over 400 steps from Siesta Public Beach, one the of the best beaches in the world. House is large and has 5 en suite bedrooms. Enormous pool with lions head fountains and hot tub overlooking the wide canal. You can tie your boat up to the sea wall, and enjoy the outdoor eating area by a man made beach overlooking the canal. All the comforts of home for large family gatherings. House has two master suites one on the ground floor and second one upstairs. Beautiful landscaping in this fabulous Siesta Key home, convenient to the Siesta tennis courts and the village. Rentals of six months or less are subject to local and state taxes.
5790 Midnight Pass Rd. #110A
Area: Siesta Key

This 2/2 Gulf & Bay ground floor unit allows you beach and pool access just outside your lanai door. This is the ultimate in casual Florida living, steps to the sugary sands of Siesta Key beach. This gated resort offers all the amenities for a fabulous vacation rental including state of the art fitness center, playground, ponds for fishing, pools, tennis courts, and shuffle board. The unit also includes a laundry room with full size washer/ dryer and a reserved carport space at your front door. . February and March are always owner occupied.

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
1321 Dockside Place #122
Area: Siesta Key
Ground Floor unit, boat and water views from your Island Get A Way.  Harbour Towne Yacht offers, tennis, pool, spa, dock.  This condo is near Siesta Keys sugar sand beaches and crystal blue waters.  Spend and evening in our Siesta Key village for a little night life.
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.
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.
567 Venice Lane
Area: Siesta Key
SIESTA KEY POOL HOME...experience Island style living. Beautifully updated kitchen with state of the art stainless steel appliances, solid wood cabinets, granite counter tops and tile floor. Open floor plan with four bedrooms and two updated bathrooms with granite counters. Relax in the large and private screened lanai with a heated pool and spa surrounded by lush tropical landscaping. Additional TV/sitting room adjacent to the fourth bedroom. Plenty of room for entertaining and comfortable seating in the dining for those large dinner parties. A paver driveway leads you to the lovely gated courtyard entry way to the front door. One mile from the world renowned SIESTA KEY BEACH with it's sugar fine sand and one mile from Siesta Village for shopping, restaurants or just a stroll. This home is available for Season or annual/furnished or unfurnished . LUXURY, ANNUAL, SEASONAL,
1321 Moonmist Drive
Area: Siesta Key
This spacious Siesta Key Condo is located in a small hide-away community that is walking distance to world famous sand beaches. Featuring two large bedrooms plus a bonus room / den, two full baths a private patio. The community has a heated pool, and a fishing pier on intercoastal waters. Also your own private garden is waiting for you to relax after a long day out in the sun. Unit is booked December 29th thru February  2018 there is a 1 month minimum rent. April through December the minimum rent is 2 weeks. Welcome to Paradise.
5663 Midnight Pass Road #407
Area: Siesta Key
Enjoy all that Siesta Key has to offer at White Sands Village across from world famous Siesta Key Beach! This two bedroom two bath unit is located on the ground floor with partial views of the Intracoastal and steps to the heated pool! Washer and Dryer in unit. Community heated pool at clubhouse. King beds in both bedrooms. Public tennis courts at the beach directly across the street. Assigned covered parking.

Showing Results 1 - 15 of 32
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