Winter Park Vacation Rentals - 225 Properties

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  1. 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...

  2. Sleeps 9, $465 to $1005/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2.5

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

  3. Sleeps 6, $315 to $915/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3.5

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

  4. Sleeps 6, $185 to $525/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1.5
    Pool

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

  5. Sleeps 4, $155 to $340/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

    Studio vacation condo at the iron horse, just steps from the winter...

  6. 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...

  7. Sleeps 9, $505 to $1590/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3.5
    Hot Tub

    This beautiful luxury home has everything you would expect in a...

  8. 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...

  9. Sleeps 2, $120 to $325/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    Nice and basic one bedroom one bathroom condo located in Winter Park...

  10. Sleeps 6, $135 to $420/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  11. Sleeps 6, $150 to $450/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

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

  12. Sleeps 4, $130 to $370/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    Updated one bedroom, one bathroom condominium in Winter Park, CO....

  13. Sleeps 6, $135 to $420/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  14. Sleeps 6, $120 to $420/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Unique and colorful Winter Park condominium close to downtown and...

  15. Sleeps 4, $120 to $325/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  16. Sleeps 10, $185 to $665/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3
    Pool

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

  17. Sleeps 6, $135 to $420/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  18. Sleeps 4, $100 to $310/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...

  19. Sleeps 6, $125 to $405/night

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

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

  20. Sleeps 9, $150 to $450/night

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

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

  21. Sleeps 8, $175 to $650/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Description and unit pictures coming soon! Weekday Weekend Weekly...

  22. Sleeps 6, $125 to $405/night

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

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

  23. Sleeps 8, $175 to $650/night

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

    This premium 3 bedroom, Hi Country Haus unit encompasses 1,023...

  24. Sleeps 4, $120 to $350/night

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

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

  25. Sleeps 4, $100 to $310/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...

  26. Sleeps 6, $125 to $405/night

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

    This downtown 2 bedroom 2 bathroom unit is on the second floor and...

  27. Sleeps 6, $135 to $420/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  28. Sleeps 6, $155 to $635/night

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

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

  29. Sleeps 10, $325 to $840/night

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

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

  30. Sleeps 6, $150 to $450/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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