Title: The Windward House 3 Bedroom Home by RedAwning - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=105398519&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # The Windward House 3 Bedroom Home by RedAwning Vacation home in Siesta Key, near Siesta Key Beach ## Photo gallery for The Windward House 3 Bedroom Home by RedAwning ![House, 3 Bedrooms | Private kitchen - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)](https://images.trvl-media.com/lodging/106000000/105400000/105398600/105398519/w3839h2160x1y0-658a25c5.jpg?impolicy=resizecrop&rw=598&ra=fit) ![House, 3 Bedrooms | Living area - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)](https://images.trvl-media.com/lodging/106000000/105400000/105398600/105398519/w3839h2160x1y0-7d23a153.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House, 3 Bedrooms | View from property - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)](https://images.trvl-media.com/lodging/106000000/105400000/105398600/105398519/w3839h2160x1y0-93701039.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House, 3 Bedrooms | Dining - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)](https://images.trvl-media.com/lodging/106000000/105400000/105398600/105398519/w3839h2160x1y0-bfa5b705.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House, 3 Bedrooms | Pool - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)](https://images.trvl-media.com/lodging/106000000/105400000/105398600/105398519/w3839h2160x1y0-7e1a89db.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies The Windward House 3 Bedroom Home by RedAwning provides amenities like an adjacent golf course and a garden. Guests can connect to free in-room WiFi. ### Entire home 3 bedrooms3 bathroomsSleeps 61696 sq ft ## Popular amenities - Pet friendly - Free WiFi - Outdoor Space ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### The Windward House 3 Bedroom Home by RedAwning Vacation home in Siesta Key, near Siesta Key Beach This smoke-free vacation home features a garden. The vacation home has 3 bedrooms and offers free WiFi and a private yard. Guests can appreciate conveniences like 2.5 bathrooms and a refrigerator, and other amenities include a coffee/tea maker and a Smart TV. Guest accommodations at this vacation home offer irons/ironing boards and ceiling fans. Smart televisions are featured in guestrooms. Guests can surf the web using the complimentary wireless Internet access (speed: 25+ Mbps). Guests can make use of the in-room refrigerators and coffee/tea makers. The recreational activities listed below are available either on site or nearby; fees may apply. ## Property amenities ### Beach - Beach nearby ### Pool/Spa - Communal pool ### Internet - Available in the house: Free WiFi ### Family friendly - Children stay free (see details) ### Food and drink - Coffee/tea maker - Oven - Refrigerator - Toaster ### Bedrooms - 3 bedrooms ### Bathroom - 2.5 bathrooms - Shampoo - Towels provided ### Entertainment - Smart TV ### Outdoor areas - Garden - Yard ### Work spaces - Laptop workspace ### Comfort - Ceiling fan - Heating ### Pets - Pet friendly - Fee: USD 332 per accommodation per stay - Service animals exempt from fees ### Suitability/Accessibility - No elevator - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - Next to a golf course ### Things to do - Cycling nearby - Horseback riding nearby - Sailing nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher ### General - Garden ## Similar properties ![Beach nearby](https://images.trvl-media.com/lodging/111000000/110680000/110675600/110675510/fb633ee4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Modern Siesta Key Condo: Family-Friendly Retreat at Midnight Cove II 424D South Village - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13&selected=110675510&PinnedHotelID=110675510&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/45000000/44130000/44124500/44124447/w1919h1279x1y1-839088d6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Anchorage Resort 7th Floor 2-Bedroom Condo w Private Balcony Beach Access South Village - Pool - Kitchen - Dryer - Free WiFi 8.4 Very good 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-12&endDate=2026-02-13&selected=44124447&PinnedHotelID=44124447&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/112000000/111690000/111687400/111687349/w1600h1199x0y1-4b6fd978.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 🦩Book Me Baby! 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Fees and deposits may not include tax and are subject to change. ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed This property accepts credit/debit cards Cashless transactions are available Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room ### We should mention This property does not have elevators ### Property is also known as The Windward House 3 Bedroom Home The Windward House 3 Bedroom Home by RedAwning Siesta Key ## About the area Located in Siesta Key, this vacation home is next to a golf course and near the beach. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Looking to enjoy an event or a game while in town? See what's happening at Ed Smith Stadium or Sarasota Kennel Club. Discover the area's water adventures with sailing nearby, or enjoy the great outdoors with cycling and horse riding. [Visit our Siesta Key travel guide](https://www.expedia.ca/Siesta-Key.dx6881) [View more Vacation homes in Siesta Key](https://www.expedia.ca/Siesta-Key-Private-Vacation-Homes.d6881-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C27.27966%2C-82.56088&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=w4YVK6KRO5rVjNW6F_WGh1y7QoI=) 5022 Windward Avenue, Siesta Key, FL, 34242 ### What's nearby - ![Southwest Florida featuring general coastal views and a beach as well as a large group of people](https://images.trvl-media.com/place/6066003/ad6a01c6-1eea-49fa-a977-77719bf71f3d.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Siesta Key Beach 14 min walk \- 1.2 km - ![North America, United States, Florida, Miami-Dade County, Miami Beach, Ocean Drive ](https://images.trvl-media.com/place/553248635976197551/cf299ff0-958b-4481-9cd5-91eeead50b5c.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Irma Beach 16 min walk \- 1.4 km - ![Aerial Drone Nokomis Beach. Gulf of Mexico on Casey Key in Nokomis Florida, United States. Red tide water.](https://images.trvl-media.com/place/553248635976194251/f4a24c93-55ea-4278-8edc-243ae0358c65.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Shell Beach 3 min drive \- 2.5 km - Siesta Key Farmers Market 11 min walk \- 0.9 km - Siesta Key Beach Playground 4 min drive \- 2.4 km ### Getting around - Sarasota-Bradenton Intl. Airport (SRQ) 30 min drive ### Restaurants - Siesta Beach Pavilion 5 min drive - Siesta Key Snack Bar 6 min drive - Circle K 3 min drive - Gilligan's Island Bar & Grill 4 min drive - Siesta Key Oyster Bar 4 min drive ## Frequently asked questions ### Is The Windward House 3 Bedroom Home by RedAwning pet-friendly? ### What time is check-in at The Windward House 3 Bedroom Home by RedAwning? ### What time is check-out at The Windward House 3 Bedroom Home by RedAwning? ### Where is The Windward House 3 Bedroom Home by RedAwning located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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