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1,825 Winter Park Holiday Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Winter Park holiday rentals from 12 rental sites including HomeAway, TripAdvisor, Expedia and more, from $25 a night.

Winter Park Information

Vacation Rentals in Winter Park

Looking for a vacation rental in Winter Park? Tripping.com has 1824 vacation rental homes available in Winter Park. You'll find 34 studios, 585 1-bedroom, 565 2-bedroom and 640 rentals with 3 or more bedrooms ranging from $25 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Winter Park is $273 while the average price of a weekly rental is $5052. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Winter Park home is $13010.

Wondering if you can bring your dog or cat along with you? There are 128 pet-friendly vacation rentals available in Winter Park. In addition to accommodating pets, Winter Park rentals offer a variety of amenities. In particular, 1637 rentals have Internet and WiFi, 1582 have TV and/or cable and 631 have a pool or hot tub.

Search properties from 12 vacation rental sites in Winter Park where the top providers in that area are HomeAway, TripAdvisor, and Expedia. There are 852 HomeAway rentals, 378 TripAdvisor short term rentals and 280 Expedia vacation rentals.