1053+ Rental Villas and Private Getaways in Windward |
  1. USA
  2. Florida
  3. Port Charlotte - Charlotte Harbor
  4. Windward

Windward Vacation Rentals & One Degree Stays Homes

About Windward Vacation Rentals

There are more than 1053 vacation rentals that are available in Windward. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Windward.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Windward, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Windward. Places to stay near Windward are 1047.12 ft² on average, with prices averaging US $322 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Windward with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Windward

Type Count
Vacation Homes 739
Villas 140
Holiday Apartments 30
Cottages 19

Use these Quick Filters to Find a Vacation Rental in Windward

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windward.

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?

There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windward:

How many vacation rentals have private pools in Windward?

There are 377 vacation rentals with private pools near Windward. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Windward are best for families?

If you are looking for a family-friendly vacation home in Windward, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward:

How many onedegreestays vacation rentals are available in Windward?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 1053 in the Windward area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Windward. 

Nearby Neighborhood (1) 
Neighborhood Property Count
Cape Haze Vacation Rentals in Florida 60

People Also Ask

There are 1053 Windward, FL Vacation Rentals

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