Company Logo
US FL Sarasota County Siesta Key Hotels

The Windward House 3 Bedroom Home by RedAwning

Updated on Jul 20, 2026

View More Pictures

The Windward House 3 Bedroom Home by RedAwning

Hotels.com logo Lowest Price $0.00 Get Booking Details

Map image for 5022 Windward Avenue SIESTA KEY, FL
Located in: SIESTA KEY, FL

A short distance from sailing, cycling, and more, this pet-friendly vacation home lets you experience it all. Make short work of the 4-minute drive to Siesta Key Beach or the 6-minute drive to Shell Beach.

Spend a day at the nearby beach, relax by the communal pool, or sip a drink in the garden of this vacation home, which also features a fitness center. For a change of scenery, come inside and enjoy the free WiFi and Smart TV.

Feel free to prepare a home-cooked meal with the oven and refrigerator, coffee maker, toaster. Bathroom amenities include towels and shampoo. Other amenities include an ironing board, a ceiling fan, and heating.

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 Stardust Event Center or Ed Smith Stadium. Discover the area's water adventures with sailing nearby, or enjoy the great outdoors with cycling and horse riding.
Get the full listing »
Popular amenities
  • fitness equipment
  • heater
  • internet
  • no smoking
  • outdoor space
  • pool
Property amenities
Internet
  • Free WiFi, with speed of 25+ Mbps
Things to do
  • Cycling nearby
  • Fitness center
  • Horse riding nearby
  • Sailing nearby
Family Friendly
  • Children stay free (see details)
Language Spoken
  • English
Room amenities Policies
Check-in
  • Check-in time starts at 4:00 PM
  • Minimum check-in age: 25
Check-out
  • Check-out before 10:00 AM
Pets
  • Pets allowed for an extra charge
  • Service animals are welcome, and are exempt from fees
Special check-in instructions
  • Cashless transactions are available
  • 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
  • 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
  • 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
  • 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
Property payment types
  • American Express
  • Diners Club
  • Discover
  • JCB International
  • Mastercard
  • Visa
Important Information
Optional extras
  • A pet fee will be chargedService animals are exempt from fees
  • The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.
You need to know
  • Cashless transactions are available
  • 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
  • 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
  • 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
  • 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
 

More Hotels in Siesta key, FL

Hotels.com logo

Days Inn by Wyndham Bradenton I-75

Days Inn by Wyndham Bradenton I-75 - Vrbo Property #
Along with an outdoor pool, this smoke-free hotel has laundry facilities and a 24-hour front desk. Free on-the-go breakfast, free WiFi in public areas, and free self parking are also provided....

Golf Course Townhome Resort Amenities 2B Luxury

Golf Course Townhome Resort Amenities 2B Luxury - Vrbo Property #
Close to cycling, this welcoming apartment brings it all within reach. If you'd like to explore the area, you can make the 6-minute drive to Premier Sports Campus at Lakewood Ranch or the 18-minute...

Pool Access! Monthly Bradenton Stay, 8 Mi to Beach

Pool Access! Monthly Bradenton Stay, 8 Mi to Beach - Vrbo Property #
Located in Bradenton, this welcoming apartment lets you experience it all. Jump into your car and make short work of the 5-minute drive to LECOM Park or the 5-minute drive to IMG Bollettieri Tennis...

Quality Inn Bradenton North I-75

Quality Inn Bradenton North I-75 - Vrbo Property #
Along with an outdoor pool, this hotel has a fitness center and a business center. Free buffet breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include...

Dog-friendly Home w/ Pool & Yard in Bradenton

Dog-friendly Home w/ Pool & Yard in Bradenton - Vrbo Property #
Located in Bradenton, this welcoming cottage brings it all within your reach. Jump into your car and make short work of the 13-minute drive to Mall at University Town Center or the 15-minute drive...

9 Mi to Coquina Beach: Home w/ Pool & BBQ

9 Mi to Coquina Beach: Home w/ Pool & BBQ - Vrbo Property #
Located in Bradenton, this welcoming cottage lets you experience it all. With convenient nearby parking, you'll be ready to make the 17-minute drive to Coquina Beach or the 21-minute drive to Bean...

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality - Vrbo Property #
While you're here, you can enjoy all the comforts of home and more, including a refrigerator and an oven, as well as a stovetop and a dishwasher. Other amenities include towels, kitchenware and...

Resort-style Condo 6 Mi to Bradenton Beach!

Resort-style Condo 6 Mi to Bradenton Beach! - Vrbo Property #
Located in Bradenton, this welcoming apartment brings it all within your reach. With convenient onsite parking, you'll be ready to make the 14-minute drive to Coquina Beach or the 24-minute drive...

'the City Oasis' Near IMG & Anna Maria Island!

'the City Oasis' Near IMG & Anna Maria Island! - Vrbo Property #
Located in Bradenton, this welcoming cottage lets you experience it all. LECOM Park is an easy 14-minute walk away, so you can leave your car at the property, which offers onsite parking, or jump...

Shorewalk Vacation Villas

Shorewalk Vacation Villas - Vrbo Property #
You'll find motorized watercraft, basketball, and more on site at this family-friendly apartment. Jump into your car and make short work of the 14-minute drive to Coquina Beach or the 24-minute...
More near Siesta Key, FL | Contact Hotels.com
goodideazs, LLC is not affiliated with the authors of this post nor is it responsible for its content, the accuracy and authenticity of which should be independently verified.