Winter Park holiday rentals
We found 564 holiday rentals — enter your dates for availability
Discover a selection of 11 homes, 14 cabins and other holiday rentals in Winter Park that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - Winter Park
Paradise Pines by AvantStay | Big Bear Home | Only 1 Mile To Snow Summit!
Sleeps 12 · 3 bedrooms · 3 bathrooms
10 out of 10
exceptional
(56 reviews)
Top rated rentals - Winter Park
Cozy Stay
10 out of 10
exceptional
(244 reviews)
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value