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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
186 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 | Half Bathrooms | Price Range |
|---|---|---|---|---|---|
| 12 Yukon Lane Townhome | 12 | 4 | 2 Full | 1 | $471.00 - $793.00 Per Night |
| 228 Mountain Willow | 8 | 3 | 2 Full | 1 | $298.00 - $550.00 Per Night |
| 25 Discovery Lane - Rendezvous | 10 | 4 | 4 Full | 0 | $460.00 - $1,950.00 Per Night |
| 33 Meadow Trail | 10 | 4 | 3 Full | 1 | $500.00 - $1,300.00 Per Night |
| 383 County Road 508 | 8 | 3 | 1 Full | 1 | $190.00 - $457.00 Per Night |
| 45 Reunion Court - Rendezvous | 10 | 3 | 3 Full | 1 | $379.00 - $629.00 Per Night |
| 47 Lookout Point - Rendezvous | 10 | 3 | 3 Full | 1 | $343.00 - $629.00 Per Night |
| 492 Golf Course Circle | 16 | 7 | 8 Full | 1 | $1,375.00 - $2,300.00 Per Night |
| 500 North Lupine | 8 | 3 | 3 Full | 0 | $309.00 - $549.00 Per Night |
| 55 Campfire - Rendezvous | 10 | 4 | 4 Full | 0 | $475.00 - $890.00 Per Night |
| 59 Jabberwocky Home | 10 | 4 | 3 Full | 0 | $374.00 - $704.00 Per Night |
| 61 Jabberwocky | 10 | 5 | 5 Full | 0 | $365.00 - $684.00 Per Night |
| 65 Bluestem | 7 | 3 | 2 Full | 1 | $327.00 - $580.00 Per Night |
| 67 Fireweed 27A | 12 | 4 | 3 Full | 1 | $385.00 - $675.00 Per Night |
| 671 Vasquez | 8 | 4 | 4 Full | 0 | $600.00 - $1,073.00 Per Night |
| 671 Vasquez 2 Bed Apartment | 4 | 2 | 2 Full | 0 | $318.00 - $600.00 Per Night |
| 71 Alder Brook Homer’s Hideaway | 10 | 3 | 3 Full | 1 | $435.00 - $875.00 Per Night |
| Alante Vista Unit 16 | 6 | 2 | 2 Full | 0 | $159.00 - $341.00 Per Night |
| Antlers At Lakota 406 | 9 | 3 | 3 Full | 1 | $340.00 - $675.00 Per Night |
| Arrow at Winter Park Unit 248 | 10 | 4 | 3 Full | 0 | $395.00 - $750.00 Per Night |
| Arrow at Winter Park Unit 254 | 9 | 3 | 2 Full | 0 | $303.00 - $549.00 Per Night |
| Arrow at Winter Park Unit 276 | 10 | 3 | 3 Full | 0 | $340.00 - $675.00 Per Night |
| Arrow at Winter Park Unit 284 | 10 | 5 | 3 Full | 0 | $440.00 - $775.00 Per Night |
| Arrow at Winter Park Unit 286 | 11 | 3 | 3 Full | 0 | $340.00 - $675.00 Per Night |
| Bear Crossing 845 | 8 | 3 | 3 Full | 1 | $385.00 - $743.00 Per Night |
| Beaver Village Unit #1712 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0111 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0131 | 8 | 3 | 2 Full | 0 | $256.00 - $457.00 Per Night |
| Beaver Village Unit #0211 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0221 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0232R | 4 | 1 | 1 Full | 0 | |
| Beaver Village Unit #0322 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0332 | 4 | 1 | 1 Full | 0 | $127.00 - $330.00 Per Night |
| Beaver Village Unit #0333 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0412 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0414 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0513 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0521 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0521R | 4 | 1 | 1 Full | 0 | $127.00 - $303.00 Per Night |
| Beaver Village Unit #0612 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0612R | 4 | 1 | 1 Full | 0 | $127.00 - $347.00 Per Night |
| Beaver Village Unit #0621 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0623 | 6 | 2 | 2 Full | 0 | |
| Beaver Village Unit #0623R | 4 | 1 | 1 Full | 0 | |
| Beaver Village Unit #0711 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0711R | 4 | 1 | 1 Full | 0 | $127.00 - $303.00 Per Night |
| Beaver Village Unit #0712 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0712R | 4 | 1 | 1 Full | 0 | $127.00 - $303.00 Per Night |
| Beaver Village Unit #0721 | 6 | 2 | 2 Full | 0 | |
| Beaver Village Unit #0723 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0724 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #0821 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #0834 | 10 | 4 | 3 Full | 0 | $247.00 - $479.00 Per Night |
| Beaver Village Unit #0922 | 7 | 2 | 2 Full | 0 | |
| Beaver Village Unit #0931 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #1022 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #1112 | 8 | 3 | 2 Full | 0 | |
| Beaver Village Unit #1113 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #1113R | 4 | 1 | 1 Full | 0 | $127.00 - $303.00 Per Night |
| Beaver Village Unit #1123 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #1124 | 10 | 4 | 3 Full | 0 | $253.00 - $534.00 Per Night |
| Beaver Village Unit #1134 | 10 | 4 | 3 Full | 0 | $253.00 - $534.00 Per Night |
| Beaver Village Unit #1531 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #1612 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #1633 | 6 | 2 | 2 Full | 0 | $162.00 - $370.00 Per Night |
| Beaver Village Unit #1714 | 6 | 2 | 2 Full | 0 | $207.00 - $389.00 Per Night |
| Beaver Village Unit #1734 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #1812 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #1821 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #1824 | 6 | 2 | 2 Full | 0 | |
| Beaver Village Unit #1923 | 6 | 2 | 2 Full | 0 | |
| Beaver Village Unit #1932 | 4 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #1934 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Beaver Village Unit #2032 | 6 | 2 | 2 Full | 0 | $188.00 - $370.00 Per Night |
| Cozens Pointe Building H Unit H301 | 6 | 2 | 2 Full | 0 | $200.00 - $387.00 Per Night |
| Cozens Pointe Building I Unit I201 | 8 | 3 | 1 Full | 0 | $265.00 - $429.00 Per Night |
| Creekside Unit 403 | 8 | 3 | 3 Full | 0 | $195.00 - $358.00 Per Night |
| Crestview Place Unit 507 | 8 | 3 | 3 Full | 0 | $230.00 - $485.00 Per Night |
| Crestview Place Unit 607 | 8 | 3 | 3 Full | 0 | |
| Dogwood Unit 8 | 6 | 2 | 1 Full | 0 | $146.00 - $325.00 Per Night |
| Fraser Crossing 3509 | 4 | 1 | 1 Full | 0 | $114.00 - $399.00 Per Night |
| Fraser Crossing 3518 | 2 | 0 | 1 Full | 0 | $121.00 - $312.00 Per Night |
| Fraser Crossing 3618 | 4 | 0 | 1 Full | 0 | $121.00 - $319.00 Per Night |
| Hi Country Haus Unit 0309 | 4 | 1 | 1 Full | 0 | $103.00 - $275.00 Per Night |
| Hi Country Haus Unit 0315 | 4 | 1 | 1 Full | 0 | $103.00 - $275.00 Per Night |
| Hi Country Haus Unit 0403 | 4 | 1 | 1 Full | 0 | $103.00 - $275.00 Per Night |
| Hi Country Haus Unit 0406 | 4 | 1 | 1 Full | 0 | |
| Hi Country Haus Unit 0705 | 6 | 2 | 1 Full | 0 | $146.00 - $341.00 Per Night |
| Hi Country Haus Unit 1413 | 4 | 1 | 1 Full | 0 | $103.00 - $275.00 Per Night |
| Hi Country Haus Unit 1503 | 4 | 1 | 1 Full | 0 | $103.00 - $275.00 Per Night |
| Hi Country Haus Unit 1515 | 4 | 2 | 1 Full | 0 | |
| Hi Country Haus Unit 1618 | 8 | 3 | 2 Full | 0 | $248.00 - $505.00 Per Night |
| Hi Country Haus Unit 1801 | 8 | 3 | 2 Full | 0 | $248.00 - $505.00 Per Night |
| Hi Country Haus Unit 1802 | 6 | 2 | 2 Full | 0 | $182.00 - $345.00 Per Night |
| Hi Country Haus Unit 1805 | 8 | 3 | 2 Full | 0 | $248.00 - $505.00 Per Night |
| Hi Country Haus Unit 1903 | 6 | 2 | 1 Full | 0 | $159.00 - $358.00 Per Night |
| Hi Country Haus Unit 1908 | 6 | 2 | 2 Full | 0 | $182.00 - $345.00 Per Night |
| Hi Country Haus Unit 1913 | 6 | 2 | 2 Full | 0 | |
| Hi Country Haus Unit 2007 | 6 | 2 | 2 Full | 0 | $182.00 - $345.00 Per Night |
| Hi Country Haus Unit 2111 | 6 | 2 | 2 Full | 0 | |
| Hi Country Haus Unit 2115 | 8 | 3 | 2 Full | 0 | $248.00 - $505.00 Per Night |
| Hi Country Haus Unit 2121 | 6 | 3 | 2 Full | 0 | |
| Hi Country Haus Unit 2201 | 6 | 3 | 2 Full | 0 | $231.00 - $455.00 Per Night |
| Hi Country Haus Unit 2203 | 6 | 2 | 2 Full | 0 | $182.00 - $345.00 Per Night |
| Hi Country Haus Unit 2501 | 4 | 1 | 1 Full | 1 | |
| Hi Country Haus Unit 2506 | 5 | 1 | 1 Full | 1 | $137.00 - $330.00 Per Night |
| Hideaway Village Alpine 4 | 6 | 2 | 2 Full | 0 | $124.00 - $279.00 Per Night |
| Hideaway Village Columbine 7 | 4 | 2 | 1 Full | 1 | $124.00 - $279.00 Per Night |
| Hideaway Village Ladora 3 | 6 | 2 | 2 Full | 0 | $141.00 - $286.00 Per Night |
| Iron Horse Building C Unit 1023 | 4 | 1 | 1 Full | 0 | $130.00 - $375.00 Per Night |
| Iron Horse Building D Unit 4104 | 4 | 1 | 1 Full | 0 | $130.00 - $375.00 Per Night |
| Iron Horse Building D Unit 5034 | 4 | 0 | 1 Full | 0 | $121.00 - $312.00 Per Night |
| Iron Horse Building D Unit 5054 | 4 | 0 | 1 Full | 0 | $91.00 - $330.00 Per Night |
| Iron Horse Building H Unit 2408 | 6 | 2 | 3 Full | 0 | $248.00 - $594.00 Per Night |
| Iron Horse Building J Unit 1309 | 9 | 2 | 1 Full | 0 | $248.00 - $594.00 Per Night |
| Kings Crossing Townhome 4 | 8 | 3 | 3 Full | 0 | |
| Leland Creek Home | 10 | 5 | 4 Full | 1 | $500.00 - $1,128.00 Per Night |
| Lion's Gate Pines Unit 101 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 102 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 103 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 104 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 105 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 106 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 108 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 109 | 8 | 3 | 2 Full | 0 | $185.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 110 | 8 | 3 | 2 Full | 0 | $185.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 111 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 112 | 9 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 113 | 6 | 2 | 1 Full | 0 | $141.00 - $319.00 Per Night |
| Lion's Gate Pines Unit 114 | 6 | 2 | 1 Full | 0 | $141.00 - $319.00 Per Night |
| Lion's Gate Pines Unit 115 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 116 | 8 | 3 | 2 Full | 0 | $185.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 117 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 118 | 8 | 3 | 2 Full | 0 | $185.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 119 | 6 | 2 | 1 Full | 0 | $124.00 - $319.00 Per Night |
| Lion's Gate Pines Unit 120 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 121 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 122 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 123 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 124 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lion's Gate Pines Unit 125 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Lookout Village A6 | 6 | 2 | 1 Full | 2 | $159.00 - $341.00 Per Night |
| Meadow Ridge Court 18 Unit 11 | 6 | 2 | 2 Full | 0 | $167.00 - $336.00 Per Night |
| Meadow Ridge Court 28 Unit 4 | 8 | 3 | 2 Full | 0 | |
| Meadow Ridge Court 28 Unit 6 | 8 | 3 | 2 Full | 0 | $191.00 - $347.00 Per Night |
| Meadow Ridge Court 8 Unit 6 | 6 | 2 | 1 Full | 0 | $141.00 - $319.00 Per Night |
| Meadow Ridge Court 9 Unit 4 | 4 | 1 | 1 Full | 0 | $104.00 - $250.00 Per Night |
| Meadowridge Court 14 Unit 1 | 8 | 3 | 2 Full | 0 | |
| Meadowridge Court 19 Unit 1 | 7 | 3 | 3 Full | 0 | $213.00 - $465.00 Per Night |
| Meadowridge Court 19 Unit 1R | 6 | 2 | 2 Full | 0 | $190.00 - $358.00 Per Night |
| Miles Behind Log Cabin | 10 | 3 | 2 Full | 0 | $500.00 - $965.00 Per Night |
| Sawmill Station Unit 111 | 8 | 3 | 3 Full | 0 | $385.00 - $743.00 Per Night |
| Silverado I Building B Unit 204 | 6 | 2 | 2 Full | 0 | $189.00 - $402.00 Per Night |
| Silverado I Building C Unit 101 | 10 | 3 | 3 Full | 0 | $224.00 - $490.00 Per Night |
| Snowblaze Condos Building A unit 33 | 8 | 3 | 3 Full | 0 | $224.00 - $480.00 Per Night |
| Snowblaze Condos Building C unit 24 | 7 | 2 | 2 Full | 0 | $189.00 - $402.00 Per Night |
| Snowblaze Condos Building E unit 310 | 4 | 0 | 1 Full | 0 | $91.00 - $235.00 Per Night |
| Telemark Townhomes Unit 582 | 9 | 4 | 3 Full | 1 | $385.00 - $743.00 Per Night |
| Timber Lake 341 | 8 | 3 | 3 Full | 0 | $303.00 - $561.00 Per Night |
| Timber Ridge Building 2, Unit B | 8 | 3 | 2 Full | 0 | $190.00 - $402.00 Per Night |
| Timber Run Aspen Unit 101 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Timber Run Aspen Unit 102 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Timber Run Cedar Unit 102 | 6 | 2 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Cedar Unit 203 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Timber Run Cedar Unit 204 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Timber Run Dogwood Unit 101 | 6 | 2 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Dogwood Unit 102 | 6 | 2 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Dogwood Unit 107 | 6 | 2 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Dogwood Unit 203 | 6 | 2 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Dogwood Unit 204 | 6 | 2 | 2 Full | 0 | |
| Timber Run Dogwood Unit 210 | 6 | 3 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Dogwood Unit 305 | 8 | 3 | 3 Full | 0 | $187.00 - $399.00 Per Night |
| Timber Run Dogwood Unit 306 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Timber Run Dogwood Unit 311 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Timber Run Evergreen Unit 101 | 6 | 2 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Evergreen Unit 102 | 6 | 2 | 2 Full | 0 | $146.00 - $292.00 Per Night |
| Timber Run Evergreen Unit 107 | 6 | 2 | 2 Full | 0 | $130.00 - $292.00 Per Night |
| Timber Run Evergreen Unit 311 | 8 | 3 | 2 Full | 0 | $187.00 - $399.00 Per Night |
| Trailhead Lodges Building 101 Unit 131 | 9 | 3 | 2 Full | 0 | $273.00 - $499.00 Per Night |
| Trailhead Lodges Building 401 Unit 422 | 6 | 2 | 2 Full | 0 | $186.00 - $387.00 Per Night |
| Trailhead Lodges Building 701 Unit 731 | 4 | 1 | 1 Full | 0 | $119.00 - $349.00 Per Night |
| Vasquez Creek Townhomes #1 | 8 | 3 | 2 Full | 0 | $168.00 - $375.00 Per Night |
| Vista Unit 16 | 4 | 0 | 1 Full | 0 | $102.00 - $264.00 Per Night |
| Vista Unit 3 | 2 | 0 | 1 Full | 0 | $79.00 - $226.00 Per Night |
| Winter Park Lodge II E304 | 6 | 2 | 1 Full | 0 | $112.00 - $319.00 Per Night |
| Winterstar Building G #3 | 6 | 2 | 2 Full | 0 |
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