186+ Rental Villas and Private Getaways in Winter Park |
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Winter Park Villa Rentals

About Winter Park Vacation Rentals

There are more than 186 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 788.27 ft² on average, with prices averaging CA $315 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 107
Holiday Apartments 44
Villas 5
Cottages 2

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, FL

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

December - February
High 38°F       Low 2°F
March - May
High 55°F       Low 18°F
June - August
High 75°F       Low 34°F
September - November
High 67°F       Low 19°F

Stay Near Winter Park's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Winter Park's Research Top Attractions For Your Vacation


Full Sail University
Rollins College
Winter Park Village
Kraft Azalea Gardens
Casa Feliz Historic Home Museum
Mead Garden
Lee Road Shopping Center
Morse Museum of American Art
Lake Virginia
Albin Polasek Museum and Sculpture Gardens
Crealde School of Art
All Fired Up
Winter Park Playhouse
Alfond Swimming Pool
Winter Park Country Club
Winter Park Corner Shopping Center
The Center of Winter Park Shopping Center
Virginia S. Nelson Rose Garden
Winter Pines Golf Club
Winter Park History Museum

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


Mead Garden 728 Properties
Hollie Anna Shopping Center 573 Properties
Lake Rose 514 Properties
Winter Park Playhouse 512 Properties
Lake Virginia 510 Properties
Alfond Swimming Pool 507 Properties
Lee Road Shopping Center 489 Properties
All Fired Up 469 Properties
Cahall Sandspur Field 460 Properties
Hannibal Square Heritage Center 458 Properties
Cornell Fine Arts Museum 456 Properties
Goldenrod 168 Properties

Complexes around Winter Park, FL


Orlandos Sunshine Orlando 3 Properties
Legacy Park 2 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 10 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 2026 is over 186 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 (6) 
Neighborhood Property Count
Northeast Orlando Rental Villas and Private Getaways in Orlando, Florida 581
College Park Rental Villas and Private Getaways in Orlando, Florida 44
Goldenrod Rental Villas and Private Getaways in Orlando, Florida 168
North Orange Rental Villas and Private Getaways in Orlando, Florida 863
Baldwin Park Rental Villas and Private Getaways in Orlando, Florida 544
Orwin Manor Rental Villas and Private Getaways in Orlando, Florida 842

People Also Ask

There are 17 hotels in Winter Park and 156 rentals

Recently Booked Hotels, Resorts, or Rentals in Winter Park