476+ Rental Villas and Private Getaways in Winter Park |
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  2. California
  3. Big Bear Lake
  4. Winter Park

Winter Park Villa Rentals

About Winter Park Vacation Rentals

There are more than 476 incredible getaway rentals that are available in Winter Park. 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 Winter Park.

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 Winter Park, 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 Winter Park. Places to stay near Winter Park are 1691.21 ft² on average, with prices averaging CA $854 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Winter Park. 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 Winter Park

Type Count
Vacation Homes 216
Cabin Rentals 185
Holiday Apartments 19
Ski Chalet Rentals 13

Use these Quick Filters to Find a Vacation Rental in Winter Park

★ 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 Winter Park with BedroomVillas.

Weather in Winter Park, CA

View the weather forecast for Winter Park before booking your Winter Park 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

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Summit Estates 431 Properties

Complexes around Winter Park, CA


Escape All Seasons Bear 16 Properties
Retreat 5 Properties
Cottage 1 Properties

Frequently Asked Questions About Winter Park?

What are the top hotels or resorts in Winter Park?

We provide an array of great vacation destinations in Winter Park. If you are looking to stay in or around the Winter Park 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 Winter Park:

How many vacation rentals have private pools in Winter Park?

We have 1 luxury villas and vacation rentals featuriung a private pool in and near Winter Park. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Winter Park is best for families?

Searching for a family-friendly getaway in Winter Park? 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 Winter Park?

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 476 in the Winter Park 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 Winter Park. 

Nearby Neighborhood (2) 
Neighborhood Property Count
Summit Estates Rental Villas and Private Getaways in Big Bear Lake, California 431
Evergreen Estates Rental Villas and Private Getaways in Big Bear Lake, California 403

People Also Ask

There are 1 hotels in Winter Park and 420 rentals

Recently Booked Hotels, Resorts, or Rentals in Winter Park