2190+ Vacation Rentals in Windsor Hills |
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  3. Orlando
  4. Windsor Hills

Windsor Hills Vacation Rentals, Hotels, & Places to Stay

About Windsor Hills Vacation Rentals

There are more than 2190 places to stay that are available in Windsor Hills. 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 Windsor Hills.

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 Windsor Hills, 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 Windsor Hills. Places to stay near Windsor Hills are 1628.06 ft² on average, with prices averaging US $351 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Windsor Hills. 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.

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Top Rental Accommodation Types in Windsor Hills

Type Count
Vacation Homes 1258
Villas 356
Holiday Apartments 223
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Windsor Hills

★ 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 Windsor Hills today.

Weather in Windsor Hills, FL

View the weather forecast for Windsor Hills before booking your Windsor Hills 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

Complexes around Windsor Hills, FL


Kissimmee 259 Properties
Orlandos Sunshine Orlando 97 Properties
Disney 16 Properties
Paradise Townhome 3 Properties
This Property 3 Properties
Almaton Loop 1 Properties
Bahama Bay Resort Davenport 1 Properties
Basnett Circle 1 Properties
Villa Daul 1 Properties

Frequently Asked Questions About Windsor Hills?

What are the top vacation rentals in Windsor Hills?

We have scoured the web to find you options in Windsor Hills. If you plan on staying near or in the Windsor Hills 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 Windsor Hills:

How many vacation rentals have private pools in Windsor Hills?

We have found 1144 places to stay that feature a private swimming pool in or near Windsor Hills. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Windsor Hills are best for families?

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

How many Varoom vacation rentals are available in Windsor Hills?

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 2190 in the Windsor Hills 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 Windsor Hills. 

Nearby Neighborhood (2) 
Neighborhood Property Count
West Kissimmee Vacation Rentals in Orlando, Florida 16641
Crestwynd Bay Vacation Rentals in Orlando, Florida 64

People Also Ask

There are 2190 Windsor Hills, FL Vacation Rentals

Recently Booked Vacation Rentals in Windsor Hills