1038+ Rental Villas and Private Getaways in Windward |
  1. USA
  2. Florida
  3. Port Charlotte - Charlotte Harbor
  4. Windward

Windward Villa Rentals

About Windward Vacation Rentals

There are more than 1038 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 1042.48 ft² on average, with prices averaging US $321 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.

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Top Private Villas, Resorts, and Rentals in Windward

Type Count
Vacation Homes 730
Villas 140
Holiday Apartments 26
Cottages 19
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windward

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Windward with BedroomVillas.

Weather in Windward, FL

View the weather forecast for Windward before booking your Windward Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

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 vacation rentals have private pools in Windward?

We have 381 luxury villas and vacation rentals featuriung a private pool in and near Windward. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Windward is best for families?

Searching for a family-friendly getaway in Windward? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

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 2025 is over 1038 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) 
Neighborhood Property Count
Cape Haze Rental Villas and Private Getaways in Florida 56

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