Entire home

The Windward House 3 Bedroom Home by RedAwning

Holiday home convenient to Siesta Key Beach

Choose dates to view prices

Where to?

Dates

February 2026

22

March 2026

House, 3 Bedrooms | Private kitchen - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)

House, 3 Bedrooms | Dining - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)

House, 3 Bedrooms | View from property - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)

House, 3 Bedrooms | Pool - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)

House, 3 Bedrooms | Living area - The Windward House 3 Bedroom Home by RedAwning (Siesta Key)

When you stay at this holiday home, you'll be within a 10-minute drive of Siesta Key Beach and Sarasota Memorial Hospital. There's also a garden, and homes offer Smart TVs and fridges.

Entire home

3 bedrooms3 bathroomsSleeps 6

Popular amenities

Pet-friendly
Free Wi-Fi
Non-smoking
Refrigerator

Main amenities (2)

Near the beach
Garden

Feel at home (5)

Children stay free
3 bedrooms
Fridge
Garden
Coffee/tea maker

Check prices for these days

Room options

Similar properties

Pool
Parking available
Free Wi-Fi
Restaurant

includes taxes & fees

23 Feb - 24 Feb

Compare similar properties

Sign in to view eligible discounts and perks. More rewards for more adventures!

Sign in Sign up, it's free

About the area

5022 Windward Avenue, Siesta Key, FL, 34242

What's nearby

Siesta Key Farmers Market - 11 min walk - 0.9 km
Siesta Key Beach - 14 min walk - 1.2 km
Irma Beach - 16 min walk - 1.4 km
Shell Beach - 2 min drive - 2.5 km
Siesta Key Beach Playground - 3 min drive - 2.4 km

Getting around

Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 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
‪Sun Garden Cafe - ‬3 min drive

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

When you stay at this holiday home, you'll be within a 10-minute drive of Siesta Key Beach and Sarasota Memorial Hospital. There's also a garden, and homes offer Smart TVs and fridges.

At a glance

Property size

- Private holiday home

Arriving/Leaving

- Check-in time starts at 4:00 PM
- Minimum check-in age – 25
- Check-out time is 10:00 AM

Special check-in instructions

- Guests will receive an email within 5 days before arrival with check-in information
- Information provided by the property may be translated using automated translation tools

Required at check-in

- Credit card, debit card or cash deposit required for incidental charges
- Government-issued photo ID may be required
- Minimum check-in age is 25

Children

- Children stay free when occupying the parent or guardian's room, using existing bedding
- No cots (infant beds)

Pets

- Pets allowed*
- Service animals welcome

Internet

- Free Wi-Fi in rooms (speed: 25+ Mbps)

Other information

- Smoke-free property

Property amenities

Beach

Near the beach

Pool/Spa

Shared/communal pool

Internet

Free Wi-Fi, with a speed of 25+ Mbps

Family friendly

Children stay for free (see details)

Food and drink

Fridge
Oven
Toaster
Coffee/tea maker

Bedrooms

3 bedrooms

Bathrooms

2.5 bathrooms
Shampoo
Towels provided

Entertainment

Smart TV

Outdoor areas

Garden
Garden

Work spaces

Laptop workspace

Comfort

Ceiling fan
Heating

Pets

Service animals exempt from fees
Pet friendly
USD 332 per accommodation per stay

Suitability/Accessibility

No lifts
Smoke-free property

Services and conveniences

Iron/ironing board

Location highlights

Next to a golf course

Things to do

Horse riding nearby
Cycling nearby
Sailing nearby

Safety features

Carbon monoxide detector installed (host has indicated that there is a carbon monoxide detector on the property)
Smoke detector installed (host has indicated that there is a smoke detector on the property)
Fire extinguisher

Fees & policies

Pets

Service animals exempt from fees
Pets are allowed for an extra charge of USD 332 per accommodation, per stay

Policies

This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room.

This property does not have lifts.

Host has indicated that there is a carbon monoxide detector on the property.

Host has indicated that there is a smoke detector on the property.

Guests can rest easy knowing that there's a fire extinguisher on-site.

This property accepts credit/debit cards.

Credit cards accepted: Visa, Mastercard, American Express, Discover, Diners Club, JCB International

Cashless transactions are available.

Also known as

The Windward House 3 Bedroom Home

The Windward House 3 Bedroom Home by RedAwning Siesta Key

Frequently asked questions

Does The Windward House 3 Bedroom Home by RedAwning offer free cancellation for a full refund?

Yes, The Windward House 3 Bedroom Home by RedAwning does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in, depending on the property's cancellation policy. Just make sure that you check this property's cancellation policy for the exact terms and conditions.