windward Windward

Windward | Siesta Key Vacation Rental

Reside at this elegant retreat for your extended stay on beautiful Siesta Key. Enjoy the islands' miles of #1 rated beaches and laidback lifestyle of Siesta Key Village within walking distance or a quick bike ride. 

This single story 4 bedroom 3 1/2 bathroom canal front home features a large swimming pool with plenty of sun lounging area around including ample private backyard space great for entertaining visiting family and friends. Arrive at this home after driving down through a quiet canal lined neighborhood street at it circular paver driveway. Stepping through the front entrance french doors you are greeted in the foyer with views straight through to the outdoor patio, pool, and 100' of waterfront. 

Adjacent to the foyer are the living room featuring a faux fireplace with access out to the patio through large sliding glass doors. This area is also furnished with a bar equipped with small beverage fridge. Enter through double doors from the living room into the study offering lounge seating and office desk. The dining room, just off of the kitchen offers seating for 8 around a round dining table. The center of the home features a gourmet kitchen with solid wood cabinetry, Wolf and Sub-Zero stainless steel appliances, and granite counters. Open to the family room with views of the pool, this most used space is a joy to cook and entertain from. 

Moving through the living room furnished with sofas and chairs for lounging and enjoying the views, equipped with large flat screen TV, you can access the guest suite. Furnished with queen-size bedroom set, TV, walk-in closet, with private bathroom. The guest suite also provides direct access to the the back yard and pool areas. Moving back through the home you can find two additional guest bedrooms sharing a jack-and-jill bathroom. One bedroom is furnished with another queen-size bedroom set while the other is furnished with two twin beds. All bedrooms are equipped with their own flat-screen TV and cable service. 

Opposite the guest wing of the home, you will find the master suite. This large bedroom offers ample space with king-size bedroom set and additional lounge seating. Directly access the pool and patio through sliding glass doors and enjoy pool and waterfront views through many bright windows in the room. Around the corner you will find an ample sized closet with custom cabinetry for your belongings and clothing. further down the hall you come to the master bathroom featuring jacuzzi tub and massage shower along with his and hers vanity spaces. 

Outside this executive home, you will find a covered patio overlooking the pool surrounded by lush tropical landscape for excellent privacy. An outdoor kitchen and seating for 8 makes this a great entertaining space weather you are grilling on the gas BBQ or lounging out by the pool. 

The home allows for access to a dock great for fishing from or parking a boat for those days out on the water. A double jet ski lift is also available for docking your jet skis. Plenty of room for a boat/jet ski trailer if you bring your own or there are many options to rent water-crafts in the area. 

Minimum Rental Requirement: 1 month minimum stay required with the exception of 2 and 1 week reservations may be considered a maximum of 60 days in advance and can only be accepted 1 time per 30-days.

Optional Fees:

Pets: $500 Non-refundable fee and prior approval required.

Pool Heating: $175/week
  Daily Weekly
7/3/20 - 7/31/20 $200 -
8/1/20 - 11/30/20 $160 -
12/1/20 - 12/31/20 $269 -
1/1/21 - 1/31/21 $322 -
2/1/21 - 2/28/21 $400 -
3/1/21 - 3/31/21 $419 -
4/1/21 - 4/30/21 $419 -
5/1/21 - 5/31/21 $169 -
6/1/21 - 7/3/21 $200 -
4 Bedrooms
3½ Baths
24Hr Check-In
Air Conditioning
Ceiling fans
Coffee Maker
Dishes Utensils
Fire Extinguisher
Free Parking
Hair Dryer
Heated Outdoor Pool Private
Iron Board
Minimum Age Limit
Smoke Detector
Smoking Not Allowed
Tennis courts nearby
Water View
Cable/satellite TV
Laptop Friendly
Sleeps: 8
Siesta Key
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Overall Rating:

5 5
Slice of Paradise
Review Date: 02/29/2020
1 5 5
Beautiful property great location love the boat dock and being able to use a boat everyday enjoyed the patio and cooking at my meals outside cool was fun to be able to cool off in.
Manager Response:
Thank you for choosing Windward on Siesta Key as your vacation rental accommodations. We are happy to hear you enjoyed your stay. Being able to use ur own boat and dock at the house is a great plus, no driving to and from a marina! The patio is a great peaceful place to enjoy the cooler mornings.
Lovely luxurious place for a group
Review Date: 01/04/2020
1 5 5
Pool, veranda, large well-equipped kitchen make this a great place to enjoy Florida weather. Property manager immediately addressed problems that arose during our two-month stay (broken pool pump, microwave). Bikes and beach equipment in the garage allow one to fully enjoy village offerings as well as the beach. Short-term guests of ours from up north very much enjoyed staying at the house.
Manager Response:
Thank you for choosing Windward for your extended stay on Siesta Key. We are happy to hear you enjoyed your stay George and look forward to accommodating you for a future visit.
Beautiful home, lovely stay
Review Date: 08/31/2019
1 5 5
We greatly enjoyed our stay at this lovely home. Everything was just as described and the accommodations were spacious and attractive. We hope to return to this property again in the future. Also, cannot say enough about the excellent property management staff at Rent Siesta Key who handled any request or query incredibly promptly--a truly top notch, professional team. Thank you to John and Richard for doing everything possible to ensure we had a terrific time on Siesta.
Manager Response:
Thanks for the excellent review Victoria! We are so happy to hear you enjoyed your stay at the Windward property on Siesta Key and we would certainly love to accommodate you on a future visit.
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