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Winter Park Summer Rentals, Cottages & Cabins

Book a Place to Stay in Winter Park for Your Summer Getaway

About Winter Park Summer Rental on Rent By Owner

With 135 summer rentals in or near Winter Park, choosing a suitable rental home for your upcoming summer getaway on Rent By Owner is easy. Whether you are traveling with family, friends, or in a group to Winter Park or areas nearby, RBO has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.

Looking for a relaxing place to stay in Winter Park for a summer vacation you do not want to forget easily? Rent By Owner summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Winter Park, RBO has got you covered for your next summer holiday.

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Frequently Asked Questions About Winter Park Luxury 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 Summer Rentals in Winter Park:

In 2025, RBO offers 135 summer rentals in or around Winter Park. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Winter Park is $236. Check the full list of summer accommodations in Winter Park.
There are 135 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rent By Owner.

Yes, here are some popular summer holiday rentals in Winter Park that have a private or indoor pool:

Check all holiday rentals with a pool in Winter Park on Rent By Owner.