Winter Park Vacation Rentals - 236 Properties

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  1. Sleeps 10, $155 to $291765/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2

    Sitting atop Forest Trail, this charming, authentic cabin exudes...

  2. Sleeps 8, $245 to $585/night

    City : Granby
    Bedrooms : 3
    Bathrooms : 3
    Hot Tub

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

  3. Sleeps 9, $150 to $350/night

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

    This expertly appointed third floor two bedroom two bathroom condo...

  4. Sleeps 4, $100 to $270/night

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

    This unit has 495 square feet with a modern decor and is an end unit...

  5. Sleeps 4, $100 to $270/night

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

    Hi Country Haus 406 is a 1 bedroom unit on the first floor and has...

  6. Sleeps 6, $155 to $490/night

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

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

  7. Sleeps 6, $110 to $250/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1
    Pool

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

  8. Sleeps 10, $185 to $525/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3
    Pool

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

  9. Sleeps 4, $15 to $270/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...

  10. Sleeps 12, $185 to $885/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  11. Sleeps 6, $15 to $17435/night

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

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

  12. Sleeps 10, $325 to $625/night

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

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

  13. Sleeps 6, $150 to $350/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  14. Sleeps 8, $185 to $430/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Gorgeous updated kitchen, open floor plan with views of dining and...

  15. Sleeps 6, $125 to $380/night

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

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

  16. Sleeps 4, $130 to $310/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  17. Sleeps 6, $135 to $350/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  18. Sleeps 6, $135 to $350/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    You will enjoy this two bedroom two bathroom Winter Park condo...

  19. Sleeps 6, $150 to $350/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This Winter Park vacation rental has a nicely updated kitchen and...

  20. Sleeps 5, $100 to $270/night

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

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

  21. Sleeps 6, $135 to $350/night

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

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

  22. Sleeps 4, $120 to $310/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  23. Sleeps 6, $135 to $350/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  24. Sleeps 9, $405 to $875/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2.5

    Enjoy this three level, vacation town home at Lakota in Winter Park,...

  25. Sleeps 6, $275 to $795/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3.5

    This 3 bedroom, 3.5 bathroom is located 1.5 miles from downtown...

  26. Sleeps 8, $570 to $1705/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3.5

    This luxury town-home is new to the rental program and conveniently...

  27. Sleeps 6, $160 to $455/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1.5
    Pool

    This 2 story vacation rental town home is located in Hideaway...

  28. Sleeps 6, $160 to $635/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This 2 bedroom, 2 bathroom condo rental is located at SnowBlaze, in...

  29. Sleeps 4, $150 to $420/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1
    Pool

    This vacation condo has 2 bedrooms, 1 bathroom and is located in...

  30. Sleeps 30, $795 to $1705/night

    City : Winter Park
    Bedrooms : 9
    Bathrooms : 9
    Pets OK Pets OK

    Ski in...Shuttle out at this Winter Park, Colorado rental home. A 9...