Winter Park Vacation Rentals - 48 Properties

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  1. Sleeps 2, $75 to $140/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

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

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

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3.5

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

  3. 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,...

  4. Sleeps 3, $125 to $340/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

    Studio vacation condo at the Iron Horse, just steps from the Winter...

  5. Sleeps 4, $160 to $455/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1.5
    Pets OK

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

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

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1

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

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

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

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

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

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3.5

    This luxury townhome is new to the rental program and conveniently...

  9. 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...

  10. Sleeps 6, $140 to $545/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

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

  11. Sleeps 8, $240 to $640/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 3

    2 bedroom vacation condo, just steps from the Winter Park ski area....

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

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3

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

  13. Sleeps 6, $150 to $645/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

    This Winter Park condo is ideal for families! Extra bedding can be...

  14. Sleeps 8, $210 to $685/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2.5

    This 3-story townhome, located in Lakota, sits on a quiet cul-de-sac...

  15. Sleeps 12, $160 to $655/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2.5

    There is no other property like this in the Beaver Village complex!...

  16. Sleeps 5, $130 to $260/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

    Welcome to Winter Park! Silverado II is right on the bus line that...

  17. Sleeps 4, $90 to $200/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1.5

    This newly remodeled unit offers a true mountain getaway in style....

  18. Sleeps 4, $45 to $180/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

    This newly renovated studio sleeps 4 comfortably with one Queen...

  19. Sleeps 4, $120 to $535/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1

    This newly built, contemporary vacation rental property is located...

  20. Sleeps 2, $125 to $340/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

    Studio vacation condo at the Iron Horse, just steps from the Winter...

  21. Sleeps 4, $115 to $295/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1

    This vacation condo is a 1 bedroom, 1 bathroom located in the Hi...

  22. Sleeps 14, $450 to $1025/night

    City : Winter Park
    Bedrooms : 6
    Bathrooms : 3
    Pets OK

    Get the real mountain experience staying at the Mary Jane Chalet...

  23. Sleeps 9, $435 to $900/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2.5

    Enjoy this three level, vacation town home in the Lakota area in...

  24. Sleeps 11, $565 to $1760/night

    City : Winter Park
    Bedrooms : 5
    Bathrooms : 5

    Dream Catcher 7B at Lakota is a luxurious 3 level vacation townhome...

  25. Sleeps 8, $240 to $640/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

    2 bedroom vacation condo at the Iron Horse Resort, just steps from...

  26. Sleeps 7, $140 to $545/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

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

  27. Sleeps 6, $150 to $640/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

    This 2 bedroom 2 bathroom vacation condo is located in Old Town...

  28. Sleeps 4, $100 to $265/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

    This comfortable vacation studio is tucked in the trees, located...

  29. Sleeps 8, $130 to $260/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

    This 2 bedroom Snowblaze condo has all you need for a fun family...

  30. Sleeps 10, $380 to $780/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2.5

    This 3BR/2.5BA corner unit offers unparalleled views of the slopes...