Winter Park Vacation Rentals - 196 Properties

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  1. Sleeps 7, $130 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Light and bright condo! You will enjoy this two bedroom two bathroom...

  2. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Bright new lighting and an updated kitchen really make this condo...

  3. Sleeps 7, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    We are sure you will enjoy this beautifully updated two bedroom two...

  4. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  6. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Newly remodeled and comfy condo will make staying in the mountains...

  7. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Nice and bright two bedroom, two bathroom condominium located in...

  8. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    Nice and bright one bedroom, one bathroom condominium located in...

  9. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    Totally remodeled one bedroom one bathroom condo featuring stainless...

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

    City : Winter Park
    Bedrooms : 4
    Bathrooms : 3
    Pool

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

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

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Cozy and comfortable three bedroom two bathroom condo located in...

  12. Sleeps 12, $185 to $670/night

    City : Winter Park
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  13. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  14. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  15. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  16. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  17. Sleeps 4, $130 to $350/night

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

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

  18. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  19. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

    We think you will enjoy this completely remodeled condo located...

  20. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

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

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  22. Sleeps 7, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  23. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  24. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  25. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

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

  26. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  27. Sleeps 6, $150 to $515/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  28. Sleeps 4, $130 to $350/night

    City : Winter Park
    Bedroom : 1
    Bathroom : 1
    Pool

    This large and spacious Winter Park one bedroom condo has all that...

  29. Sleeps 10, $330 to $1245/night

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

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

  30. Sleeps 8, $245 to $955/night

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

    This three level town home located in Winter Park Colorado is just...