The Windward House

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The Windward House

Siesta Key, FL

3 Bedrooms 2 full, 1 half Baths 6 Guests 1696 sq. ft. Pets OK
(5.0)

Welcome to your slice of paradise on Siesta Key, where luxury meets comfort in this completely refurbished Mid-Century Modern vacation home just minutes from the stunning beaches. Nestled in a serene neighborhood, this dog-friendly retreat offers a seamless blend of style, functionality, and relaxation.

- Gorgeous Canal-Front Mid-Century Modern Home
- Pet Friendly
- Heated Pool
- Private Canal Access with Boat Dock
- Fenced In Backyard
- Pool Loungers
- Gas Grill
- Golf Cart Rental Available
- 5-7 Minute Drive to Siesta Key Main Access
- Fully Stocked Kitchen
- Office Space with High Speed Internet
- Free Trolley Service
- Quiet Neighborhood
- Spacious Indoor / Outdoor Layout
- 4 Minutes to Siesta Key Village
- 4 Minutes to Top Dining Options

As you step inside, you're greeted by the timeless allure of terrazzo floors that flow gracefully throughout the open floor plan, enhancing the home's mid-century charm. The attention to detail and abundance of natural light create an inviting ambiance that sets the stage for a memorable stay.

The heart of the home is a harmonious fusion of form and function. In the living room, a cozy fireplace invites you to unwind on a plush sectional sofa, while a large SMART TV stands ready to entertain. The dining room, kitchen, and living area flow together effortlessly, adorned with iconic mid-century modern furniture and clean lines that exude style.

Slide open the ceiling-to-floor glass doors, and you'll step into your own private oasis with a fenced in yard that opens to the canal. The outdoor living space beckons with modern furnishings, a heated pool glistening invitingly, and a courtyard adorned with sun loungers – the perfect spot to soak up the Florida sun. And with direct access to the deep-water canal leading to Sarasota Bay, aquatic adventures are just a stone's throw away.

Back inside, the gourmet kitchen awaits the culinary enthusiast. A large island with stools invites casual dining and conversation, while stainless steel appliances stand ready to bring your culinary creations to life. A kitchen nook boasts a wine cooler, coffee station, and full-size washer and dryer, ensuring convenience at every turn.

Retreat to the primary bedroom through the adjacent office, where a king-size bed adorned with plush linens promises a restful night's sleep. Enjoy direct access to the pool area for a refreshing morning swim or a midnight dip under the stars. The ensuite bathroom boasts a spacious glass walk-in shower and a vanity with two sinks, providing a spa-like experience.

Guests will find their own slice of paradise in the well-appointed bedrooms. A queen-sized bed graces one room, complete with a SMART TV for entertainment. In the second guest bedroom, two twin beds offer flexible sleeping arrangements, also accompanied by a SMART TV. The guest bathroom features a sleek glass walk-in shower, while a convenient half bath is located just down the hall.

Throughout the home, contemporary design elements harmonize with the natural surroundings, creating a seamless transition between indoor and outdoor living spaces. Whether you're seeking relaxation, adventure, or simply a stylish sanctuary to call your own, this Mid-Century Modern haven on Siesta Key promises an unforgettable escape.

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The Beauty of Siesta Key
Siesta Key is a barrier island positioned between the Gulf and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids.

The Siesta Key Village offers a wide selection of shops, cafes, top restaurants, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate. Trolley transportation is available around the island and throughout Sarasota.

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Please note:

The yard is fenced in but does open up to the canal.

This is a pet friendly home and allows up to 2 dogs. Please include your pet in your booking so we can make the appropriate departure cleaning arrangements. A $125 pet fee is required to help with the departure cleaning to remove pet hair and dander from any furnishings and floors for our future guests. Dogs are not allowed in the pool at any time as the filtration system is not designed for filtering pet hair. Thank you for your understanding and cooperation!

Pool Heater: We recommend only heating the pool in the months of October through May, as the pool during summer months should not need heating. If you’d like the pool heated during your stay, please let us know 48 hours or more before your arrival so we can have it ready for you. A $12 daily heating fee applies to help cover energy costs. Please note, if you request heating after check-in, a $50 service fee will be added for our team to come out and activate the heater. Dogs are not allowed in the pool at any time as the filtration system is not designed for filtering pet hair. Thank you for your understanding—we want to ensure you enjoy a comfortable and relaxing swim!

Rooms

Primary Bedroom

1 King

Guest Bedroom

1 Queen

Guest Bedroom

2 Twin

Amenities

Location & Attractions

  • Car - Not Necessary
  • Family Themed
  • Marina
  • Museums
  • Ocean Nearby
  • Zoo
  • Bay
  • Beach Access
  • Health Beauty Spa
  • Romantic Themed
  • View - Water
  • Waterfront

Bedroom & Laundry

  • Wardrobe or Closet
  • Bed Linens
  • Essentials
  • Extra Pillows & Blankets
  • Hangers
  • Iron & Ironing Board
  • Dryer - Private
  • Washer - Private

Cleanliness & Safety

  • Common Surfaces Disinfected
  • Deadbolt Lock
  • Disinfectant Used While Cleaning
  • Fire Extinguisher
  • Outdoor Lighting
  • Carbon Monoxide Detector
  • Linens High Temp Wash (140 degrees)
  • Self Check-In & Check-Out
  • Smoke Detector
  • First Aid Kit

Sports, Leisure & Adventure

  • Eco Tourism
  • Antiquing
  • Bird Watching
  • Boating
  • Cycling
  • Diving
  • Fishing
  • Fishing - Bay
  • Fishing - Deep Sea
  • Fishing - Fly
  • Fishing - Freshwater
  • Fishing - Pier
  • Fishing - Surf
  • Golf
  • Horseback Riding
  • Jet Skiing
  • Outlet Shopping
  • Parasailing
  • Sailing
  • Shopping
  • Snorkeling
  • Swimming
  • Wildlife Viewing
  • Wind Surfing

Bathroom

  • Body Soap
  • Conditioner
  • Hair Dryer
  • Hot Water
  • Shampoo
  • Shower Gel
  • Towels
  • Cleaning Products

Entertainment

  • TV
  • Smart TV

Internet & Office

  • Ethernet Connection
  • Laptop Friendly Workspace
  • Wifi
  • Wifi - Free
  • Wifi - Speed 500mbps
  • Desk
  • Desk Chair
  • Office

Kitchen & Dining

  • Baking Sheet
  • BBQ Grill Utensils
  • Coffee
  • Coffee Maker
  • Cooking Basics
  • Dining Area or Room
  • Dining table
  • Dishes & Silverware
  • Freezer
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Blender
  • Dishwasher
  • Hot Water Kettle
  • Kitchen Island
  • Spices
  • Wine Glasses

Other Building, Complex Or Neighborhood Amenities

  • Hospital

Other Property Amenities

  • Air Conditioning
  • Ceiling Fan
  • Heating
  • Private Entrance
  • Courtyard - Private
  • Ground Floor
  • Living Room
  • Pets - Allowed
  • Single Level Home

Parking & Facilities

  • Parking - Free
  • Parking - On Site Free
  • Parking - Private

Services

  • Concierge - Available

Accessibility

  • Bedroom - Step Free Access
  • Common Space - Step Free Access
  • Flat Smooth Pathway to Front Door
  • Home - Step Free Access

Outdoor

  • BBQ Grill Area
  • BBQ Grill - Gas
  • BBQ Grill - Private
  • Beach Essentials
  • Bicycle
  • Fenced Yard
  • Garden or Backyard
  • Outdoor Dining
  • Outdoor Seating & Furniture
  • Outdoor Shower
  • Patio or Balcony
  • Sun Loungers
  • Veranda

Pool & Spa

  • Pool
  • Pool - Heated
  • Pool - Private
See All Amenities +

Reviews

5.0
(9 Reviews)
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Manuela
Stayed Aug, 2026
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Everything was perfect

Beautiful house, amazing beach and host always answered my questions quickly. We had a great time!
Stephanie
Stayed Jul, 2026
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Great stay. Perfect location. Nice design.

Pool was lovely. Been coming to Siesta Key to visit family for over 30 years and usually stay on the beach. This was such a nice change. Highly recommend. A+
Jennifer
Stayed Jul, 2026
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This was a great place!

The enclosed back patio and pool area has tall bushes that provide privacy, which I appreciate.
Brandyn
Stayed Jun, 2026
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Great location and outdoor space

Our second time staying at this home- love the location and the outdoor space!
Arcadio
Stayed Jun, 2026
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Amazing

We had an amazing time at this house. It was a pleasant surprise to see it included beach chairs, umbrella, and other beach toys. Also they left toiletries and even cooking spices. Much appreciated. We spent a lot of time at the pool. It has a sound system in and outside of the house so we played our music while in the pool or bbqing. It\'s a short 5-min drive to Siesta Key beach, 15-min to Sarasota downtown and 20-min to Lido Beach. Would come back to this property again.
Kendyll
Stayed May, 2026
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Enjoyed this property!

About a 15-20 minute walk to the beach. Bikes available on site as well as renting the golf cart to make it easy to get around. Parking around the area is mostly paid parking. Great restaurants, bars, ice cream and shopping near by. Home was clean, stocked and well appointed for our needs. Pool and canal access was great. Host was easy to work with. Would recommend and stay again.
Kathryn
Stayed Apr, 2026
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This was the perfect vacation home!

It was so comfortable and beautiful and close that everything. We didn’t want to leave. We brought our dog, the yard is fully fenced and we could let her out without any concerns.
Chris
Stayed Dec, 2025
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Great location

Great location and house had everything you could need. Ability to rent golf cart on site was a nice addition.
Kimberly
Stayed Dec, 2025
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Perfect!!

This was a lovely and family friendly home with lots of open space, close to town and and a lovely back yard on the water. Dog friendly too - with a secure fenced in area. The back yard on the water was an added plus - we saw dolphin and within the lovely persimmon tree - filled with native air plants - an owl perched directly above our heads while we sat outside watching the sunset. The house was within walking distance to Mortons’ (the best market in town), and multiple beach access. This was a perfect location and I miss it already so much

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