Winter Park Vacation Rentals - 66 Properties

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  1. 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...

  2. 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,...

  3. 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...

  4. 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...

  5. 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...

  6. Sleeps 6, $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...

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

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

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

  8. 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...

  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 8, $295 to $640/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 3
    Pool

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

  11. Sleeps 10, $265 to $705/night

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

    Everyone from snow bunnies to black diamond pros can find runs to...

  12. 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...

  13. Sleeps 7, $170 to $320/night

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

    Key Info Bedrooms: 2 # Full Baths: 2 Sleeps in Beds (not counting...

  14. Sleeps 10, ~$1025/night

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

    This spacious three bedroom luxury townhouse with over 2000 square...

  15. Sleeps 4, $80 to $425/night

    City : Winter Park
    Bedrooms : 2
    Bathroom : 1

    Nestled in the the pines in a downtown, this warm, charming,...

  16. Sleeps 4, $145 to $1485/night

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

    This condo is located in building 7 and close to the clubhouse that...

  17. Sleeps 8, $250 to $670/night

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

    Nice and bright three bedroom three bathroom Winter Park condo....

  18. Sleeps 4, $130 to $335/night

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

    A beautifully remodeled kitchen has new wood cabinets, granite...

  19. 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...

  20. 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...

  21. 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...

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

    City : Winter Park
    Bedroom : studio
    Bathroom : 1

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

  23. Sleeps 4, $145 to $285/night

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

    1 bedroom, 1 bath with a comfortable sofa sleeper in the living...

  24. 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...

  25. Sleeps 14, ~$1930/night

    City : Winter Park
    Bedrooms : 5
    Bathrooms : 4.5
    Hot Tub

    Fabulous 5-BR Luxury Home in Lakota, Views. Perfect for 2 families....

  26. Sleeps 8, ~$1145/night

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

    This luxury 3-bedroom, 3 bath, one-level condo is located in...

  27. Sleeps 6, $120 to $260/night

    City : Winter Park
    Bedrooms : 2
    Bathrooms : 2

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

  28. Sleeps 9, $145 to $310/night

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

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

  29. Sleeps 8, $285 to $510/night

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

    Absolutely incredible luxurious home nestled in the woods...

  30. Sleeps 10, $225 to $860/night

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

    Looking for a family-friendly group getaway in Winter Park? This...