Windward, FL Villa Rentals

We compare villas and rental homes from owners across Booking.com, Vrbo and Expedia.

Destination
Dates
Guests
Search
  • Up-front pricing
  • No markup
  • Trusted partners

Compare Villas, Resorts, & Rentals in Windward

1,280 villas and rentals
Sort by
See More Properties

About Windward Vacation Rentals

There are more than 1280 incredible getaway rentals that are available in Windward. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Windward.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Windward, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Windward. Places to stay near Windward are 1158.63 ft² on average, with prices averaging US $386 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Windward. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Hotels in Windward and 1084 rentals

Recently Booked Hotels, Resorts, or Rentals in Windward

Frequently Asked Questions About Windward?

What are the top hotels or resorts in Windward?

We provide an array of great vacation destinations in Windward. If you are looking to stay in or around the Windward area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windward:

How many hotels, resorts, or rentals are available in Windward?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 1280 in the Windward area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Windward. 

Nearby Neighborhood (1)

NeighborhoodProperty Count
Cape Haze Rental Villas and Private Getaways in Florida 59