Winter Park Vacation Rentals - 159 Properties

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  1. Sleeps 2, $65 to $160/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

    This charming studio sits on top of the hill with gorgeous views...

  2. Sleeps 7, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This classic Winter Park two bedroom condo has all that you need for...

  3. Sleeps 10, $330 to $1245/night

    City : Fraser
    Bedrooms : 3
    Bathrooms : 4
    Pool Hot Tub

    Winter Park cabin or home? Families, couples or singles will love...

  4. Sleeps 4, $110 to $335/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1.5
    Pool Hot Tub

    A 1 bedroom Hi Country Haus Winter Park condo is a very comfortable...

  5. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

    This wonderful two bedroom two bathroom Winter Park condo has been...

  6. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    This classic Winter Park one bedroom condo has all that you need for...

  7. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This classic Winter Park two bedroom condo has all that you need for...

  8. Sleeps 6, $125 to $435/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1
    Pool Hot Tub

    A Colorado condo vacation rental is a lovely decorated 2 bedroom...

  9. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    This classic Winter Park one bedroom condo has all that you need for...

  10. Sleeps 6, $145 to $510/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Hot Tub

    This Winter Park Colorado condo offers 899 square feet and is on the...

  11. Sleeps 8, $245 to $955/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3.5
    Pool Hot Tub

    This three level town home located in Winter Park Colorado is just...

  12. Sleeps 12, $185 to $670/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Contemporary furnishings, decor and accessories take you back to the...

  13. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    Nice and bright one bedroom, one bathroom condominium located in...

  14. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Nice and bright two bedroom, two bathroom condominium located in...

  15. Sleeps 10, $195 to $740/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3
    Pool

    Tons of space and a lot of light! This four bedroom three bathroom...

  16. Sleeps 6, $160 to $670/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Hot Tub

    This Winter Park ski condo rental has 1,006 square foot unit is on...

  17. Sleeps 8, $245 to $955/night

    City : Granby
    Bedrooms : 3
    Bathrooms : 3
    Hot Tub

    A 3 bedroom 3.5 bathrooms town home with three interior levels and...

  18. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This modern two bedroom two bathroom Winter Park condo feels...

  19. Sleeps 6, $110 to $350/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1
    Pool

    A lovely townhome with 880 square feet of living space on two...

  20. Sleeps 6, $145 to $510/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

    This condo rental for skiing in Winter Park is a ground floor condo...

  21. Sleeps 6, $125 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This classic Winter Park two bedroom condo has all that you need for...

  22. Sleeps 10, $515 to $2135/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3.5

    If you’re looking for the ultimate log cabin get away, then look...

  23. Sleeps 4, $110 to $335/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    This unit is non-smoking and no pets allowed unit and has been...

  24. Sleeps 4, $105 to $650/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    Ready, set, relax! Trailhead Lodge 811 is a beautifully appointed...

  25. Sleeps 7, $130 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    A warm interior will greet you as you enter this lovely updated two...

  26. Sleeps 8, $185 to $670/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Large and spacious Winter Park condo, conveniently located close to...

  27. Sleeps 4, $110 to $335/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Hot Tub

    Bright cheery tones and warm wood finishes will entice your senses...

  28. Sleeps 6, $125 to $435/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1
    Hot Tub

    A Winter Park ski area in Colorado rental on the second floor in...

  29. Sleeps 5, $110 to $335/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1.5
    Pool Hot Tub

    A 1 bedroom vacation rental with 629 square feet, this unit is...

  30. Sleeps 8, $185 to $670/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Cozy and comfortable three bedroom two bathroom condo located in...