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 33
Name
Area
Description
6285 Midnight Pass Road #107
Area: Siesta Key
Come and relax in this bright end unit condo. This 2 bedroom 2 bath condo has its own washer and dry. The master bath has just been completed updated. The complex has a community room and exercise room on bayside/game room/2 lighted tennis courts/pickle ball courts. Private beach access, heated swimming pools, saunas, spas, outdoor grills, showers and picnic areas. Enjoy your morning coffee on the lanai with partial view of intercostal. Condo available now till Dec 31, 2017 for two weekly rental or monthly. Owners uses condo in Season.
1208 Solitude Lane
Area: Siesta Key
Fantastic house on Siesta Key near the village and the world famous beach. Three bedrooms plus office and upstairs loft. No elevator. Relax on the porch watching a flat screen TV overlooking the pool/spa and canal. Lift and dock.
1640 Summerhouse Lane #10
Area: Siesta Key
Arrive in style in your own private elevator to this luxurious condo on sought after Siesta Key. This condo boasts 3 bedrooms, 2 1/2 baths and over 2200 sq feet and is located behind the gates at Summer Cove. This luxurious condo has been professionally decorated. The amenities include state of the art fitness center, billiards room, community center, heated community pool, dock and most importantly access to the World Famous Siesta Key Beach located directly across the street! 20 minutes to downtown Sarasota with all that has to offer. Fine dining, boutique shopping, the arts, opera etc. Also walking distance to Siesta Key Village which is always a fun time. Located on the south end of the key is perfect as it offers easy access to and from the Island. This is the perfect spot for your winter get-away!
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!
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!!
  
710 Treasure Boat Way
Area: Siesta Key
Easy bike ride or walk to Siesta Village. This well-kept home is perfect for outdoor entertaining by the pool. Open floor plan and large kitchen/family room. Enjoy Siesta Beach just minutes away.
4660 Ocean Blvd. #B2
Area: Siesta Key
Sea Village is a beautifully landscaped residential community on 5 acres overlooking the blue-green waters of the Gulf of Mexico. Located on the 2nd floor, this 3 bedroom unit shows like a model! It is completely renovated with bamboo floors, granite counters, 42" cabinets and stainless steel appliances. The Master bedroom suite has a walk in closet and a stackable washer/dryer. This is a serene and quiet complex with 2 pools, a fishing pier and an outdoor fire pit. The carport is located in front of the unit and plenty of guest parking is available. Walking distance to Siesta Key Beach and the Village for shopping, dining and entertainment. Owner will rent off-season, annually or seasonally. No pets permitted.
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.
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
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 

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.
1257 S. Portofino Drive #105
Area: Siesta Key
Newly listed ground floor rental at Siesta Harbor on Siesta Key comes with a boat slip right outside your door. 1 bedroom/2 bath unit with gorgeous views of the Boat Harbor and the Intracoastal Waterway. Enjoy the many social events at the clubhouse or head to the beach across the street. Take a stroll to the shops and restaurants at the South Village or take a free hop on shuttle to Siesta Key Village for more fun and entertainment. Your reserved carport is just steps away from your front door. This is a 55+ community. Special pricing for 5 month bookings, December - April. No pets allowed.
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. 
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.

Showing Results 1 - 15 of 33
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