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Winter Park Family Rentals & Large Homes

Find Family-Friendly Vacation Rentals Near Winter Park

About Winter Park Family Rental on PickleTrip

Looking to stay in Winter Park and play pickleball with your family in your downtime? Look no further than PickleTrip™! We offer a variety of affordable pickleball-friendly accommodations including vacation rentals, resorts, and hotels with private courts on-site or nearby.

While we are known for our premium pickleball stays, we also offer a variety of other great properties for your stay. Choose from boutique hotels, cozy cottages, lakefront villas, and more. Many of our properties are located in prime pickleball destinations so you can spend your days playing the sport you love.

Traveling with your family or a group of pickleball enthusiasts? No problem! We have the perfect accommodations for you. From spacious villas to comfortable condos, we have plenty of room for your family and friends to stay and play. Stay and play pickleball when you travel with PickleTrip™!

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Frequently Asked Questions About Winter Park Family Rentals

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

The average price per night for a family holiday rental in Winter Park is $260. Check the list of kid-friendly accommodations in Winter Park.
There are 155 2-bedroom rental properties that are available in Winter Park. You can book for your next trip with PickleTrip.
Yes, here are some top-rated family vacation rentals in Winter Park that have a private swimming pool:

Check all holiday rentals with a pool in Winter Park on PickleTrip.

Yes, We have 155 direct by owner rentals in Winter Park.
Yes, Of course! There are many luxury rental properties in or near Winter Park. Use our search filter to discover all of our luxury homes with your favorite amenities. Sorting by price is another way to find the luxury holiday rentals in Winter Park, though more expensive is not always better.