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All Winter Park Vacation Rentals

Explore our wonderful collection of vacation rentals to get the most from your Winter Park vacation.   

Stay Winter Park offers easy online booking process and our dedicated staff can assist you 7 days a week by calling 1-800-215-6535. 


All Winter Park Vacation Rentals

175 properties listed.

# A B C D E F G H I J K L M N O P Q R S T U V W X Y Z

Property Sleeps Bedrooms Bathrooms Price Range
12 Yukon Lane Townhome 10 4 2 Full $410.00 - $793.00 Per Night
25 Discovery Lane - Rendezvous 10 4 4 Full $400.00 - $660.00 Per Night
383 County Road 508 8 3 1 Full $215.00 - $315.00 Per Night
45 Reunion Court - Rendezvous 10 3 3 Full $330.00 - $629.00 Per Night
47 Lookout Point - Rendezvous 8 3 3 Full $330.00 - $629.00 Per Night
492 Golf Course Circle 16 7 8 Full $1,375.00 - $2,100.00 Per Night
55 Campfire - Rendezvous 10 4 4 Full $468.00 - $660.00 Per Night
61 Jabberwocky 10 5 5 Full $365.00 - $684.00 Per Night
671 Vasquez 8 4 4 Full $625.00 - $1,128.00 Per Night
671 Vasquez 2 Bed Apartment 4 2 2 Full $250.00 - $660.00 Per Night
Alante Vista Unit 16 6 2 2 Full $154.00 - $341.00 Per Night
Antlers At Lakota 406 9 4 3 Full $315.00 - $675.00 Per Night
Arrow at Winter Park Unit 248 10 4 3 Full $425.00 - $684.00 Per Night
Arrow at Winter Park Unit 284 10 5 3 Full $425.00 - $545.00 Per Night
Arrow at Winter Park Unit 286 11 3 3 Full $340.00 - $599.00 Per Night
Bear Crossing 845 8 3 3 Full $360.00 - $743.00 Per Night
Beaver Village Unit #1712 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #1712R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0111 6 2 2 Full $162.00 - $358.00 Per Night
Beaver Village Unit #0131 8 3 2 Full $190.00 - $468.00 Per Night
Beaver Village Unit #0211 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0221 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0221R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0224 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0224R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #0232R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0322 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0333 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0333R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0412 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0412R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0513 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0521 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0521R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #0612 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0612R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0621 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0621R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0623 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0623R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #0711 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0711R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #0712 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0712R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #0721 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0721R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0723 6 2 2 Full $162.00 - $358.00 Per Night
Beaver Village Unit #0724 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0821 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0833 8 3 2 Full $190.00 - $468.00 Per Night
Beaver Village Unit #0834 10 4 3 Full $215.00 - $479.00 Per Night
Beaver Village Unit #0922 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0922R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #0931 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #0931R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #0934 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #0934R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #1022 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #1112 8 3 2 Full $190.00 - $468.00 Per Night
Beaver Village Unit #1113 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1113R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #1123 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #1123R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #1124 10 4 3 Full $220.00 - $534.00 Per Night
Beaver Village Unit #1134 10 4 2 Full $215.00 - $479.00 Per Night
Beaver Village Unit #1612 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #1612R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #1633 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1633R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #1713 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1713R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #1724 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #1734 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1734R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #1812 6 2 2 Full $162.00 - $356.00 Per Night
Beaver Village Unit #1814 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1814R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #1821 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1824 6 2 2 Full $170.00 - $389.00 Per Night
Beaver Village Unit #1824R 4 1 1 Full $155.00 - $347.00 Per Night
Beaver Village Unit #1923 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1923R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #1932 6 2 2 Full $162.00 - $356.00 Per Night
Beaver Village Unit #1934 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #1934R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #2023 6 2 2 Full $160.00 - $356.00 Per Night
Beaver Village Unit #2023R 4 1 1 Full $140.00 - $303.00 Per Night
Beaver Village Unit #2032 6 2 2 Full $162.00 - $356.00 Per Night
Beaver Village Unit #2032R 4 1 1 Full $139.70 - $303.00 Per Night
Crestview Place Unit 507 8 3 3 Full $275.00 - $429.00 Per Night
Founders Pointe 4646 4 1 1 Full $155.00 - $419.00 Per Night
Fraser Crossing 3618 4 0 1 Full $140.00 - $355.00 Per Night
Hi Country Haus Unit 0315 4 1 1 Full $121.00 - $275.00 Per Night
Hi Country Haus Unit 0403 4 1 1 Full $121.00 - $275.00 Per Night
Hi Country Haus Unit 0406 4 1 1 Full $121.00 - $275.00 Per Night
Hi Country Haus Unit 0501 6 2 1 Full $154.00 - $358.00 Per Night
Hi Country Haus Unit 0503 4 1 1 Full $121.00 - $275.00 Per Night
Hi Country Haus Unit 0611 6 2 1 Full $132.00 - $341.00 Per Night
Hi Country Haus Unit 0705 6 2 1 Full $132.00 - $341.00 Per Night
Hi Country Haus Unit 1013 8 3 1 Full $177.00 - $356.00 Per Night
Hi Country Haus Unit 1016 2 1 1 Full $143.00 - $330.00 Per Night
Hi Country Haus Unit 1503 4 1 1 Full $121.00 - $275.00 Per Night
Hi Country Haus Unit 1515 4 2 1 Full $132.00 - $341.00 Per Night
Hi Country Haus Unit 1618 8 3 2 Full $197.00 - $468.00 Per Night
Hi Country Haus Unit 1801 8 3 2 Full $197.00 - $468.00 Per Night
Hi Country Haus Unit 1802 6 2 2 Full $165.00 - $345.00 Per Night
Hi Country Haus Unit 1805 8 3 2 Full $197.00 - $468.00 Per Night
Hi Country Haus Unit 1903 6 2 1 Full $154.00 - $358.00 Per Night
Hi Country Haus Unit 1908 6 2 2 Full $165.00 - $345.00 Per Night
Hi Country Haus Unit 1913 6 2 2 Full $165.00 - $345.00 Per Night
Hi Country Haus Unit 2003 6 2 1 Full $132.00 - $341.00 Per Night
Hi Country Haus Unit 2007 6 2 2 Full $165.00 - $345.00 Per Night
Hi Country Haus Unit 2111 6 2 2 Full $165.00 - $345.00 Per Night
Hi Country Haus Unit 2121 6 3 2 Full $197.00 - $468.00 Per Night
Hi Country Haus Unit 2201 6 3 2 Full $176.00 - $440.00 Per Night
Hi Country Haus Unit 2203 6 2 2 Full $165.00 - $345.00 Per Night
Hi Country Haus Unit 2501 4 1 1 Full $121.00 - $275.00 Per Night
Hi Country Haus Unit 2506 4 1 1 Full $143.00 - $330.00 Per Night
Hideaway Village Alpine 4 6 2 1 Full $125.00 - $250.00 Per Night
Hideaway Village Columbine 3 2 1 1 Full $110.00 - $209.00 Per Night
Hideaway Village Columbine 7 4 2 1 Full $125.00 - $250.00 Per Night
Iron Horse Building C Unit 1023 4 1 1 Full $121.00 - $413.00 Per Night
Iron Horse Building D Unit 4104 4 1 1 Full $121.00 - $413.00 Per Night
Iron Horse Building D Unit 5034 4 0 1 Full $135.00 - $355.00 Per Night
Iron Horse Building D Unit 5054 4 0 1 Full $135.00 - $330.00 Per Night
Iron Horse Building H Unit 2408 6 2 3 Full $230.00 - $594.00 Per Night
Jabberwocky Home 10 4 2 Full $360.00 - $704.00 Per Night
Kings Crossing Townhome 4 8 3 3 Full $205.00 - $495.00 Per Night
Leland Creek Home 10 5 4 Full $470.00 - $1,128.00 Per Night
Lion's Gate Pines Unit 120 8 3 2 Full $200.00 - $440.00 Per Night
Lookout Village A6 6 2 2 Full $145.00 - $341.00 Per Night
Meadow Ridge Court 18 Unit 11 6 2 2 Full $171.00 - $336.00 Per Night
Meadow Ridge Court 28 Unit 4 8 3 2 Full $185.00 - $435.00 Per Night
Meadow Ridge Court 28 Unit 6 8 3 2 Full $185.00 - $435.00 Per Night
Meadow Ridge Court 8 Unit 4 6 2 2 Full $171.00 - $336.00 Per Night
Meadow Ridge Court 8 Unit 6 6 2 1 Full $145.00 - $319.00 Per Night
Meadow Ridge Court 9 Unit 4 4 1 1 Full $127.00 - $242.00 Per Night
Meadowridge Court 14 Unit 1 8 3 2 Full $185.00 - $435.00 Per Night
Meadowridge Court 19 Unit 1 7 3 3 Full $226.00 - $440.00 Per Night
Meadowridge Court 19 Unit 10 8 3 2 Full $185.00 - $435.00 Per Night
Meadowridge Court 19 Unit 1R 6 2 2 Full $180.00 - $387.00 Per Night
Miles Behind Log Cabin 10 3 2 Full $435.00 - $965.00 Per Night
Sawmill Station Unit 111 8 3 3 Full $360.00 - $743.00 Per Night
Silverado I Building B Unit 204 6 2 2 Full $154.00 - $402.00 Per Night
Snowblaze Condos Building A unit 33 8 3 3 Full $210.00 - $468.00 Per Night
Snowblaze Condos Building C unit 24 7 2 2 Full $180.00 - $387.00 Per Night
Telemark Townhomes Unit 582 9 4 3 Full $358.00 - $704.00 Per Night
Timber Lake 341 8 3 3 Full $285.00 - $561.00 Per Night
Timber Ridge Building 2, Unit B 8 3 2 Full $176.00 - $402.00 Per Night
Timber Run Aspen Unit 101 8 3 2 Full $180.00 - $440.00 Per Night
Timber Run Aspen Unit 102 8 3 2 Full $180.00 - $440.00 Per Night
Timber Run Cedar Unit 102 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Cedar Unit 203 8 3 2 Full $180.00 - $440.00 Per Night
Timber Run Cedar Unit 204 8 3 2 Full $180.00 - $440.00 Per Night
Timber Run Dogwood Unit 101 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Dogwood Unit 102 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Dogwood Unit 107 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Dogwood Unit 108 6 2 1 Full $165.00 - $303.00 Per Night
Timber Run Dogwood Unit 203 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Dogwood Unit 204 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Dogwood Unit 210 6 3 2 Full $165.00 - $303.00 Per Night
Timber Run Dogwood Unit 305 8 3 3 Full $180.00 - $440.00 Per Night
Timber Run Dogwood Unit 306 8 3 2 Full $180.00 - $440.00 Per Night
Timber Run Dogwood Unit 311 8 3 2 Full $180.00 - $440.00 Per Night
Timber Run Evergreen Unit 101 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Evergreen Unit 102 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Evergreen Unit 107 6 2 2 Full $165.00 - $303.00 Per Night
Timber Run Evergreen Unit 311 8 3 2 Full $180.00 - $440.00 Per Night
Timber Run Vista Unit 103 2 0 1 Full $110.00 - $226.00 Per Night
Timber Run Vista Unit 207 4 1 1 Full $145.00 - $275.00 Per Night
Timber Run Vista Unit 316 4 0 1 Full $132.00 - $264.00 Per Night
Trailhead Lodges Building 401 Unit 422 6 2 2 Full $180.00 - $387.00 Per Night
Vasquez Creek Townhomes #1 8 3 2 Full $170.00 - $336.00 Per Night
Winter Park Lodge II E304 6 2 2 Full $116.00 - $319.00 Per Night
Winterstar Building G #3 6 2 2 Full $160.00 - $358.00 Per Night