1135+ Vacation Rentals in Windward |
  1. USA
  2. Florida
  3. Port Charlotte - Charlotte Harbor
  4. Windward

Windward Vacation Rentals, Hotels, & Places to Stay

About Windward Vacation Rentals

There are more than 1135 places to stay that are available in Windward. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Windward.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. 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 Varoom's places in Windward, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Windward. Places to stay near Windward are 1046 ft² on average, with prices averaging US $344 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Windward. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Show more
Show less

Top Rental Accommodation Types in Windward

Type Count
Vacation Homes 800
Villas 144
Holiday Apartments 30
Cottages 18

Use these Quick Filters to Find a Vacation Rental in Windward

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Windward today.

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 vacation rentals in Windward?

We have scoured the web to find you options in Windward. If you plan on staying near or in the Windward area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay in Windward:

How many vacation rentals have private pools in Windward?

We have found 418 places to stay that feature a private swimming pool in or near Windward. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Windward are best for families?

If you are looking for a place to stay that is family-friendly in Windward, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Windward:

How many Varoom vacation rentals are available in Windward?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2026 is over 1135 in the Windward area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Windward. 

Nearby Neighborhood (1) 
Neighborhood Property Count
Cape Haze Vacation Rentals in Florida 66

People Also Ask

There are 1135 Windward, FL Vacation Rentals

Recently Booked Vacation Rentals in Windward