The Windward House

Holiday hom5022 Windward Avenue, Siesta Key, FL, United StatesShow on map

You won’t be charged yet

Check-in from 4:00 PMCheck-out by 10:00 AM.
Free parkingThe property states parking on site is free for guests.

The Windward House is a luxurious beachfront property in Siesta Key, offering a private pool and balcony access. With 3 bedrooms, a fully equipped kitchen, and private entrance, this holiday home is perfect for a relaxing getaway.

Spacious Accommodation: Enjoy the comfort of 3 bedrooms and 2 bathrooms, along with a TV and modern amenities.

Private Pool and Balcony: Relax by the private pool or take in the stunning views from the balcony overlooking the beach.

Convenient Location: Explore nearby attractions like The Ringling Museum of Art and Sarasota Opera, just a short drive away.

What this place offers

WiFi available
Free WiFi
Parking
Free Parking
Air conditioning
Swimming pool
Heating
Garden
BBQ facilities
Fishing

Rooms

Where you’ll be

5022 Windward Avenue, Siesta Key, FL, United States

Things to know

Cancellation

Each room shows its own terms before you pay.

Most rates can be cancelled free until a date shown on the room.

Non-refundable rates are marked as such.

House rules

Check-in from 4:00 PM

Check-out by 10:00 AM

Children welcome

No pets

Free parking on site

Payment & property

Paid when you book, not at the desk.

Rates include the taxes and fees we can read.

The property may take a card at check-in for incidentals.

What we’d check for you here

Whether there is room for a pickup, a trailer or a van, not just a car.
Whether the rate moves for your dates, and what it includes.
What the property actually charges at the desk on top of the rate.

Questions about The Windward House

What time is check-in and check-out at The Windward House?

Check-in is from 4:00 PM. Check-out is by 10:00 AM. If you're arriving late, tell us and we'll ask the property to hold the room.

Does The Windward House allow pets?

No — the property states that pets are not allowed.

Is there parking at The Windward House?

Yes — the property states that parking on site is free. Whether a space can be reserved in advance varies, so we check it against your dates.

Does The Windward House have a pool?

Yes — a pool is listed among the property's facilities. Seasonal closures are common, so we'll confirm it's open for your dates.

Does The Windward House have Wi-Fi?

Yes — internet access is listed among the property's facilities.

How do I book The Windward House?

Put your dates in above and book online, or call (888) 789-8585 and we'll do it for you — including things a booking form can't handle, like a block of rooms, a monthly rate or an invoice for your employer.

Where is The Windward House?

5022 Windward Avenue, Siesta Key, FL.

Guest review categories are not on this page yet — the supplier gives an overall score but no breakdown for this property, and we would rather show nothing than invent the bars. Call (888) 789-8585 and we’ll read you what the property says.