187+ Vacation Rentals in Winter Park |
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Winter Park Vacation Rentals, Hotels, & Places to Stay

About Winter Park Vacation Rentals

There are more than 187 places to stay that are available in Winter Park. 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 Winter Park.

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 Winter Park, 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 Winter Park. Places to stay near Winter Park are 787.51 ft² on average, with prices averaging US $229 a night.

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

Type Count
Vacation Homes 107
Holiday Apartments 45
Villas 5
Cottages 2

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

★ 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 Winter Park today.

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

Top Attractions Around Winter Park, FL

Varoom offers a large selection of top attractions around Winter Park . Research things to do on your vacation before you visit Winter Park.


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

Other Places to Stay in Winter Park, FL


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 vacation rentals in Winter Park?

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

How many vacation rentals have private pools in Winter Park?

We have found 15 places to stay that feature a private swimming pool in or near Winter Park. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Winter Park are best for families?

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

How many Varoom vacation rentals are available in Winter Park?

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 187 in the Winter Park 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 Winter Park. 

Nearby Neighborhood (6) 
Neighborhood Property Count
Northeast Orlando Vacation Rentals in Orlando, Florida 581
College Park Vacation Rentals in Orlando, Florida 44
Goldenrod Vacation Rentals in Orlando, Florida 168
North Orange Vacation Rentals in Orlando, Florida 863
Baldwin Park Vacation Rentals in Orlando, Florida 544
Orwin Manor Vacation Rentals in Orlando, Florida 842

People Also Ask

There are 187 Winter Park, FL Vacation Rentals

Recently Booked Vacation Rentals in Winter Park