Winter Park Vacation Rentals - 47 Properties

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  1. Sleeps 3, $150 to $340/night

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

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

  2. Sleeps 8, $295 to $640/night

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

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

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

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

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

  4. Sleeps 4, $165 to $420/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1
    Pool

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

  5. Sleeps 30, $865 to $1705/night

    City : Winter Park
    Bedrooms : 9
    Bathrooms : 9

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

  6. Sleeps 6, $160 to $545/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  7. 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,...

  8. 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...

  9. Sleeps 8, $680 to $1705/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3.5

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

  10. 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...

  11. 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...

  12. Sleeps 2, $90 to $165/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

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

  13. Sleeps 7, $215 to $345/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3.5

    Come bring the family and enjoy this Downtown Winter Park townhome...

  14. Sleeps 4, $110 to $155/night

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

    Iron Horse is located at the base of the mountain between Winter...

  15. Sleeps 9, $120 to $590/night

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

    The Timber Run complex is located 1 mile from downtown Winter Park...

  16. Sleeps 13, $330 to $1030/night

    City : Granby
    Bedrooms : 4
    Bathrooms : 3
    Pool

    You will be sure to enjoy Ridgetop House, a beautiful custom log...

  17. Sleeps 4, $150 to $340/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1
    Pool

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

  18. Sleeps 4, $135 to $310/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

    This studio condo is located at SnowBlaze in downtown Winter Park,...

  19. Sleeps 2, $115 to $310/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1
    Pool

    This studio condo rental is located at SnowBlaze in downtown Winter...

  20. Sleeps 8, $205 to $575/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    This beautiful 3-bedroom, 2-bathroom condo is located in Hi Country...

  21. Sleeps 8, $310 to $680/night

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

    Located near the town of Winter Park, Colorado, this premier...

  22. Sleeps 4, $150 to $340/night

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

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

  23. Sleeps 8, $325 to $910/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3.5

    This magnificent 3 bedroom plus loft area / 3.5 bathroom Penthouse...

  24. Sleeps 6, $120 to $300/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

    This condo is nestled in the Pine Tree Plaza building, directly...

  25. Sleeps 8, $325 to $910/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3

    This 3 bedroom, 3 bathroom two level vacation condo is located in...

  26. Sleeps 4, $130 to $355/night

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

    Welcome to 4368 Founders Pointe.  This property is ideal for a...

  27. Sleeps 8, $435 to $1365/night

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

    This 3 bedroom, 3.5 Bathroom condo is located at Red Quill Village...

  28. Sleeps 4, $130 to $1485/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  30. Sleeps 5, $130 to $180/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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