Winter Park holiday lettings
We found 517 holiday rentals — enter your dates for availability
Discover a selection of 14 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
Big Sky by Destination Big Bear: Luxury Log Cabin! Hot Tub! Pool Table! Fire Pit! 2 Primary Suites! Dog Friendly! A/C! Forest Walks! Arcade! EV Charger!
Sleeps 10 · 4 bedrooms · 4+ bathrooms
- 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value