Winter Park holiday rentals

We found 1,919 holiday rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Select from 533 houses, 966 flats and other holiday rentals to find the perfect place for your stay in Winter Park. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Houses

Houses
  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore destinations around Winter Park

More Holiday Rentals ideas

West Newfield Holiday Rentals
Standard Link for West Newfield
Big Bear Lake Holiday Rentals
Standard Link for Big Bear Lake
Hilton Head Holiday Rentals
Standard Link for Hilton Head
Fort Myers Holiday Rentals
Standard Link for Fort Myers
Palm Desert Holiday Rentals
Standard Link for Palm Desert
Emerald Isle Holiday Rentals
Standard Link for Emerald Isle
Kill Devil Hills Holiday Rentals
Standard Link for Kill Devil Hills
Orange Beach Holiday Rentals
Standard Link for Orange Beach
Sevierville Holiday Rentals
Standard Link for Sevierville
Huntingdon Holiday Rentals
Standard Link for Huntingdon
Carolina Beach Holiday Rentals
Standard Link for Carolina Beach
Jekyll Island Holiday Rentals
Standard Link for Jekyll Island
Sanibel Holiday Rentals
Standard Link for Sanibel
Isle of Palms Holiday Rentals
Standard Link for Isle of Palms
Sarasota Holiday Rentals
Standard Link for Sarasota
Pigeon Forge Holiday Rentals
Standard Link for Pigeon Forge
Princeville Holiday Rentals
Standard Link for Princeville
Gatlinburg Holiday Rentals
Standard Link for Gatlinburg
Saratoga Springs Holiday Rentals
Standard Link for Saratoga Springs
Davenport Holiday Rentals
Standard Link for Davenport
Surfside Beach Holiday Rentals
Standard Link for Surfside Beach
Long Pond Holiday Rentals
Standard Link for Long Pond
Bethany Beach Holiday Rentals
Standard Link for Bethany Beach
Myrtle Beach Holiday Rentals
Standard Link for Myrtle Beach
Cape May Holiday Rentals
Standard Link for Cape May
Longboat Key Holiday Rentals
Standard Link for Longboat Key
Steamboat Springs Holiday Rentals
Standard Link for Steamboat Springs
Destin Holiday Rentals
Standard Link for Destin
Broken Bow Holiday Rentals
Standard Link for Broken Bow
Charlevoix Holiday Rentals
Standard Link for Charlevoix