0 Bedrooms for 1 Guest
Price $10 - $1000+

3,023 Winter Park Holiday Rentals, Houses & Apartments

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 11 rental sites including HomeAway, TripAdvisor, PerfectPlaces, and more, ranging from $25 to $16420 a night. 
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    Information about Winter Park

    Vacation Rentals in Winter Park

    Find the best Winter Park vacation rentals with Tripping.com. Choose from 2,953 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $16420 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 2,279 of homes in Winter Park offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 1,050 rentals with pool or jacuzzi, or relax with the family in one of the 2,115 homes with cable TV.

    For all those dog lovers and cat lovers, Winter Park offers 157 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 11 rental sites in Winter Park where the top providers in that area are HomeAway, TripAdvisor, and PerfectPlaces. There are 1,296 HomeAway rentals, 420 TripAdvisor short term rentals and 416 PerfectPlaces vacation rentals.