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Winter Park Vacation Rentals - 208 Properties

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  1. Sleeps 4, $111 to $418/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1
    Pool

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

  2. Sleeps 4, $108 to $327/night

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

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

  3. Sleeps 9, $386 to $1004/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2.5

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

  4. Sleeps 8, $533 to $1703/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3.5

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

  5. Sleeps 9, $463 to $1588/night

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

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

  6. Sleeps 6, $313 to $913/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3.5

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

  7. Sleeps 6, $108 to $634/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  8. Sleeps 10, $151 to $675/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2

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

  9. Sleeps 8, $180 to $680/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  10. Sleeps 6, $148 to $448/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  11. Sleeps 6, $116 to $324/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  12. Sleeps 7, $148 to $448/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  13. Sleeps 6, $148 to $448/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  14. Sleeps 10, $180 to $664/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3
    Pool Hot Tub

    **Please note: The clubhouse pool and hot tubs will be closed from...

  15. Sleeps 6, $132 to $416/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  16. Sleeps 6, $132 to $416/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  17. Sleeps 6, $132 to $416/night

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

    **Please note: The clubhouse pool and hot tubs will be closed from...

  18. Sleeps 14, $159 to $626/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    **Please note: The clubhouse pool and hot tubs will be closed from...

  19. Sleeps 13, $191 to $740/night

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3
    Pool

    **Please note: The clubhouse pool and hot tubs will be closed from...

  20. Sleeps 4, $126 to $367/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    **Please note: The clubhouse pool and hot tubs will be closed from...

  21. Sleeps 4, $97 to $308/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...

  22. Sleeps 6, $124 to $405/night

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

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

  23. Sleeps 4, $97 to $308/night

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

    A Winter Park ski deal, this unit has 572 square feet, on the ground...

  24. Sleeps 4, $116 to $324/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    **Please note: The clubhouse pool and hot tubs will be closed from...

  25. Sleeps 7, $124 to $405/night

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

    ***Please also note that Building 19 does not permit smoking outside...

  26. Sleeps 6, $124 to $405/night

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

    A 3rd floor vacation condo rental has 899 square feet of living...

  27. Sleeps 6, $167 to $621/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 3

    A stunning remodeled 2 bedroom with loft 2.75 bathroom unit on the...

  28. Sleeps 4, $116 to $324/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    **Please note: The clubhouse pool and hot tubs will be closed from...

  29. Sleeps 5, $119 to $346/night

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

    This newly renovated vacation rental is the perfect place to unwind...

  30. Sleeps 6, $124 to $405/night

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

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