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2026-07-01
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Winter Park Vacation Rentals

Cozy Condo In Winter Park - On Blue Bus Route - Walk To Downtown, Restaurants, Grocery

114 Hi Country Dr Unit 10, Winter Park, United States Show map

Cozy Condo In Winter Park - On Blue Bus Route - Walk To Downtown, Restaurants, Grocery is located 4.2 km from Pioneer Express and 19 minutes' walk from the Cooper Creek Square. More

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Winter Haus, Winter Park 2 Bedrooms Corner Unit W Outdoor Patio Walking Distance To The Center Of Town

273 High Country Drive Unit 11, Winter Park, United States Show map

1-room Winter Haus, Winter Park 2 Bedrooms Corner Unit W Outdoor Patio Walking Distance To The Center Of Town is located in Winter Park, approximately 15 minutes on foot from the Vasquez Peak… More

From US$ 230 Book Now

Ski-In / Ski-Out Studio Condo At The Base Of Winter Park

580 Winter Park Drive 4671, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at 1-room Ski-In / Ski-Out Studio Condo At The Base Of Winter Park, which is only 1.1 km from Alpine Slide and around a 10-minute ride from Eskimo Express.… More

From US$ 161 Book Now

Iron Horse Building C Unit 1023

Winter Park, United States Show map

The 52 m² Iron Horse Building C Unit 1023 Villa Winter Park is located in Winter Park, just 0.8 km from Cabriolet, and boasts a hot tub. The apartment features Wi-Fi throughout the property. More

From US$ 237 Book Now

Ski-In / Ski-Out 1 Bedroom Condo Base Of Wp Resort

580 Winter Park Drive 4673, Winter Park, United States Show map

Overlooking the mountain, the 52 m² Ski-In / Ski-Out 1 Bedroom Condo Base Of Wp Resort Winter Park is only an 11-minute walk from Cabriolet in Winter Park. At this 1-bedroom apartment, Wi-Fi and… More

From US$ 294 Book Now

Hot Tub Steps To Dining And Ski Shuttle

78415 U.S. 40 Unit 2, Winter Park, United States Show map

The spacious 124 m² Hot Tub Steps To Dining And Ski Shuttle Winter Park apartment is a mere 400 metres from the Cozens Ranch House Museum and welcomes guests with a Jacuzzi. The Foundry Cinema and… More

From US$ 254 Book Now

Great Location! Downtown Wp With Hot Tub! Sleeps 6!

79050 U.S. 40 309, Winter Park, United States Show map

The spacious 2-bedroom Great Location! Downtown Wp With Hot Tub! Sleeps 6! Apartment Winter Park is located 3.3 km from Prospector Express and offers Wi-Fi for either business or leisure. This 84 m²… More

From US$ 308 Book Now

Beaver Village Unit #0724

193 Gcr 702 #3-204 Or 193 Village Dr #3-204, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at Beaver Village Unit #0724 Winter Park apartment, which is merely 1.3 km from Idlewild Distillery and around 25 minutes' walk from Rollins Pass. The… More

From US$ 276 Book Now

Cozy Downtown Condo With Jacuzzi 5 Min To Resort

78321 U.S. Highway 40, Winter Park, United States Show map

Cozy Downtown Condo With Jacuzzi 5 Min To Resort Winter Park is located 3.4 km from the Elizabeth Kurtak Art Gallery and 16 minutes' walk from Winter Park Jazz Festival. Wi-Fi and complimentary… More

From US$ 217 Book Now

Ski-In/Ski-Out Zephyr 1 Bedroom Condo Winter Park

201 Zephyr Way 2208, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 1-room Ski-In/Ski-Out Zephyr 1 Bedroom Condo Winter Park, which is 3.2 km from Eagle Wind and around 10 minutes by car from the Riflesight Notch. More

From US$ 358 Book Now

Hi Country Haus Unit 0309

382 Hi Country Dr #9, Winter Park, United States Show map

The 1-room Hi Country Haus Unit 0309 Apartment Winter Park is located in Winter Park, approximately 1 km from Idlewild Distillery, and pampers guests with a Jacuzzi. Fraser Tubing Hill is around a 10… More

From US$ 540 Book Now

Snowblaze Condos Building C Unit 24

Winter Park, United States Show map

Snowblaze Condos Building C Unit 24 Winter Park is located only a 7-minute walk from The Foundry Cinema and Bowl and 4.7 km from the Moffat Tunnel. This apartment boasts a hot tub and a sauna… More

From US$ 658 Book Now

Beaver Village Unit #0131

40 Village Dr #1-301, Winter Park, United States Show map

Staying at Beaver Village Unit #0131 Winter Park villa, guests can easily reach the Amaze'n Mazes Colorado, located approximately a 10-minute drive away. More

From US$ 774 Book Now

Iron Horse Studio W/ Resort Amenities; Walk To Wp!

101 Ironhorse Way, Winter Park, United States Show map

The family-friendly Iron Horse Studio With Resort Amenities Walk To Wp! Winter Park is located 4.7 km from the Cooper Creek Square and 11 minutes' walk from the Amaze'n Mazes Colorado. Offering… More

From US$ 237 Book Now

Crestview Place Unit 507

Winter Park, United States Show map

Crestview Place Unit 507 Winter Park apartment is located 7 minutes' walk from Idlewild Distillery and entices guests with a Jacuzzi. This apartment features Wi-Fi throughout the property. More

From US$ 384 Book Now

Guest Suite Downtown Winter Park Great Location

79050 U.S. 40 309A, Winter Park, United States Show map

The 23 m² Guest Suite Downtown Winter Park Great Location is located 4.3 km from the Elizabeth Kurtak Art Gallery and offers Wi-Fi for either business or leisure. This 1-bedroom apartment features a… More

From US$ 185 Book Now

Timber Run Evergreen 9

143 Forest Trail, #9, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the spacious Timber Run Evergreen 9 Winter Park apartment, which is around 25 minutes' walk from The Foundry Cinema and Bowl and approximately 4 km from… More

From US$ 116 Book Now

Beaver Village Unit #0332

124 Village Dr #332, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 1-room Beaver Village Unit #0332 Winter Park apartment, which is 3.7 km from Fraser Tubing Hill and approximately 10 minutes by car from Looking… More

From US$ 567 Book Now

Cozy Ski-In/Out Winter Park Studio W/ Hot Tubs!

313 Iron Horse Way Unit C2033, Winter Park, United States Show map

Cozy Ski-In/Out Winter Park Studio W/ Hot Tubs! is located 2.7 km from Prospector Express and 10 minutes by car from Eskimo Express. This apartment features Wi-Fi throughout the property. More

From US$ 749 Book Now

Snowblaze Condos Building E Unit 310 By Stay Winter Park

79114 Us Hwy 40, Winter Park, United States Show map

Overlooking the mountain, the 41 m² Snowblaze Condos Building E Unit 310 By Stay Winter Park is 4.3 km from the Coca Cola Tubing Hill at Winter Park in Winter Park. This 1-bedroom apartment features… More

From US$ 628 Book Now

Beaver Village

50 Village Dr 8-22, Winter Park, United States Show map

The 102 m² Beaver Village Winter Park apartment is located 3.3 km from Looking Glass and around a 25-minute walk from the Saint Bernard of Montjoux Catholic Church. This 2-bedroom apartment features… More

From US$ 240 Book Now

Beaver Village Unit #0232R

44 Village Drive Unit 232, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 1-room Beaver Village Unit #0232R Winter Park apartment, which is 2.9 km from Endeavour Lift and around a 10-minute ride from the Winter Park Resort… More

From US$ 350 Book Now

Trailhead Lodges 821

Trailhead Lodges Building 801 Unit 821 801 Trailhead Circle #821, Winter Park, United States Show map

The 74 m² Trailhead Lodges 821 Winter Park apartment is located 6 minutes' walk from the Hideaway Park and looks out onto the mountain. Wi-Fi is provided for both business and leisure activities. More

From US$ 640 Book Now

Comfy In Crestview Place

Winter Park, United States Show map

Comfy In Crestview Place Winter Park apartment offers easy access to such tourist sites as the Cooper Creek Square, located nearly 5 minutes' walk away. More

From US$ 93 Book Now

Beaver Village Unit #0623R

195 Gcr 702 #2-203 Or 195 Village Dr #2-203, Winter Park, United States Show map

Beaver Village Unit #0623R Winter Park apartment is located 3.5 km from Fraser Tubing Hill and 10 minutes' drive from the Ski Idlewild. This apartment features Wi-Fi throughout the property. More

From US$ 534 Book Now

Hi Country Happiness

518 Hi Country Dr, Building 8, Unit 4, Winter Park, United States Show map

Offering spa facilities such as a Jacuzzi and an indoor pool, Hi Country Happiness Apartment is situated around 15 minutes' walk from Saint Bernard of Montjoux Catholic Church. This 2-bedroom… More

From US$ 196 Book Now

Hi Country Haus 11-2

247 Hi Country Dr #211, Winter Park, United States Show map

The 45 m² Hi Country Haus 11-2 Apartment Winter Park is located 4.4 km from Endeavour Lift and just a 12-minute walk from the Cozens Ranch House Museum. This 1-bedroom apartment features a heated… More

From US$ 219 Book Now

Condo Winter Park Pool Hot Tub Hideaway Park

501 Trailhead Circle, Winter Park, United States Show map

Condo Winter Park Pool Hot Tub Hideaway Park is 2.5 km from the Cozens Ranch House Museum, giving access to numerous sites in the area. More

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Walk To Dtwn: Winter Park Studio W/ Hot Tub Access

79114 U.S. Hwy 40 Unit E202, Winter Park, United States Show map

Offering a swimming pool, Walk To Dtwn Winter Park Studio With Hot Tub Access is located merely a 5-minute walk from the Hideaway Park. This apartment features Wi-Fi throughout the property. More

From US$ 207 Book Now

Hi Country Haus Unit 1908

159 Hi Country Dr #1908, Winter Park, United States Show map

The 2-room Hi Country Haus Unit 1908 Apartment Winter Park is located in Winter Park, about 1 km from the Cozens Ranch House Museum, and pampers guests with a Jacuzzi. Fraser Tubing Hill is… More

From US$ 274 Book Now

Beaver Village Unit #0521R

197 Gcr 702 #1-201 Or 197 Village Dr #1-201, Winter Park, United States Show map

Beaver Village Unit #0521R Winter Park apartment is located 3.4 km from Olympia Express and a 10-minute drive from Zephyr Express. This apartment features Wi-Fi throughout the property. More

From US$ 234 Book Now

Fraser Crossing Founders Pointe, Condo - 2 Bedroom Select Unit 4440

307 S Lake Park Blvd. Unit 104, Winter Park, United States Show map

The 2-room Fraser Crossing Founders Pointe, Condo - 2 Bedroom Select Unit 4440 Winter Park is situated in Winter Park, 17 minutes' walk from Gemini Express, and offers spa amenities such as a hot tub… More

From US$ 865 Book Now

Best Location In Downtown Winter Park

79050 U.S. Hwy 40 308, Winter Park, United States Show map

Located just a 7-minute walk from the Vasquez Peak Wilderness, the 111 m² Best Location In Downtown Winter Park apartment is 3.8 km from a top family-friendly place like the Amaze'n Mazes Colorado. More

From US$ 526 Book Now

Ski Idlewild

144 Ski Idlewild Rd Building C #3209, Winter Park, United States Show map

Set approximately 10 minutes by car from Elizabeth Kurtak Art Gallery, the 2-room Ski Idlewild comprises an adjoining terrace and a balcony overlooking the mountain. Featuring a Jacuzzi, this… More

From US$ 330 Book Now

Beaver Village Unit #1134

203 Gcr 702 #1134 Or 203 Village Dr #1134, Winter Park, United States Show map

Beaver Village Unit #1134 Winter Park apartment is located in Winter Park, a 25-minute walk from the Cozens Ranch House Museum, and pampers guests with a Jacuzzi and a sauna. This apartment features… More

From US$ 619 Book Now

Beaver Village Unit #0412

128 Village Dr #4-102, Winter Park, United States Show map

Beaver Village Unit #0412 Winter Park apartment is located 3.5 km from the Moffat Tunnel and a 10-minute ride from the History Park. This apartment features Wi-Fi throughout the property. More

From US$ 400 Book Now

Hi Country 11-13

247 High Country Drive, Building 11, Unit 13, Winter Park, United States Show map

The 1-room Hi Country 11-13 Apartment Winter Park is located in Winter Park, nearly a 5-minute drive from Be.. Boutique, and offers guests a heated swimming pool and a fitness room. 3.1 km from the… More

From US$ 204 Book Now

Zephyr Mountain Ski-In Ski-Out Condo

201 Zephyr Way #2321, Winter Park, United States Show map

Zephyr Mountain Ski-In Ski-Out Condo Winter Park is located only 150 metres from Arrow Lift and only an 11-minute walk from the Coca Cola Tubing Hill at Winter Park. This apartment is situated in… More

From US$ 308 Book Now

Beaver Village Unit #0823

191 Village Drive #823 Building 8 Unit 823 2Nd Level, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at Beaver Village Unit #0823 Winter Park apartment, which is 3.9 km from the outdoor sports store "Colorado Adventure Park" and about a 10-minute ride from… More

From US$ 320 Book Now

Hi Country Haus 14-5

477 High Country Drive Building 14 Unit 5, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 1-room Hi Country Haus 14-5 Apartment Winter Park, which is 4.7 km from Endeavour Lift and within 20 minutes' walk of the Cooper Creek Square. For… More

From US$ 132 Book Now

The Sanctuary Bldg 5 #7-8

400 Hi Country Dr, Building 5, Unit 507, Winter Park, United States Show map

The 2-room The Sanctuary Bldg 5 #7-8 Apartment Winter Park is located in Winter Park, only 13 minutes' stroll from the Cozens Ranch House Museum, and offers guests a swimming pool and a fitness suite… More

From US$ 98 Book Now

Hi Country 9-3

Winter Park, United States Show map

Hi Country 9-3 Apartment Winter Park is located a 10-minute ride from Endeavour Lift and 4.9 km from Eskimo Express Chairlift. More

From US$ 146 Book Now

Beaver Village 15-11

210 Village Dr 15-11, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 2-room Beaver Village 15-11 Winter Park apartment, which is within 10 minutes' drive of Fraser Snow Tubing and 3.5 km from the Ski Idlewild. A… More

From US$ 164 Book Now

Winter Park Chalet I Mtn Biking I Summer Festivals

189 Village Drive Building 9, Unit 09-13, Winter Park, United States Show map

The spacious Winter Park Chalet I Mtn Biking I Summer Festivals is situated in Winter Park, 3.5 km from the Main Street, and offers spa amenities such as a hot tub, a sauna, and an indoor pool. Wi-Fi… More

From US$ 366 Book Now

Trailhead Lodges Building 101 Unit 131

101 Trailhead Cir #131, Winter Park, United States Show map

The 2-room Trailhead Lodges Building 101 Unit 131 Winter Park apartment is located a mere 6 minutes on foot from the Cooper Creek Square and looks out onto the city. Endeavour Lift is 3.6 km away… More

From US$ 1011 Book Now

Rustic Relaxation In Winter Park

124 Village Dr, Building 3, Unit 03-31, Winter Park, United States Show map

Rustic Relaxation In Winter Park Apartment includes a terrace and is situated merely a 5-minute walk from Cabriolet. The spacious apartment with a Jacuzzi and an indoor pool is within easy reach of… More

From US$ 557 Book Now

Winter Park Mountain Gem

Winter Park, United States Show map

Set nearly a 10-minute ride from Fraser Valley Library, the spacious 2-bedroom Winter Park Mountain Gem Apartment comprises an adjoining terrace and a balcony overlooking the mountain. The apartment… More

From US$ 209 Book Now

Silverado II Unit 334

490 Kings Crossing Road, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 2-room Silverado II Unit 334 Winter Park apartment, which is 3.2 km from the outdoor sports store "Colorado Adventure Park" and around 10 minutes by… More

From US$ 345 Book Now

Beaver Village Unit #0211

44 Gcr 702 #2-211 Or 44 Village Dr #2-211, Winter Park, United States Show map

Located about 10 minutes' drive from the Winter Park Resort, the 79 m² Beaver Village Unit #0211 Winter Park apartment is 3.5 km from a top family-friendly place like the Amaze'n Mazes Colorado. This… More

From US$ 448 Book Now

Fun + Cozy Winter Park Condo, 3.5 Miles To Resort

90 Hideaway Drive 2, Winter Park, United States Show map

Located 4.1 km from Winter Park Resort, the spacious 83 m² Fun + Cozy Winter Park Condo, 3.5 Miles To Resort features private car parking for those who travel by car. 3.6 km from the 2-bedroom… More

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