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2026-11-14
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Vacation Rentals in Winter Park

Winter Park Condo W/ Hot Tubs, 4 Min To Ski Resort

Winter Park, CO, 80482, Winter Park, United States Show map

The 2-bedroom Winter Park Condo W/ Hot Tubs, 4 Min To Ski Resort villa is located within 25 minutes' walk of Cozens Ranch House Museum and provides a Jacuzzi. The welcoming holiday home can host 7… More

From US$ 144 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

Fraser Crossing Founders Pointe, Condo - 2 Bedroom Select Unit 4440 Winter Park offers easy access to such tourist sites as Amaze'n Mazes Colorado Amusement Center, located about 5 minutes' walk away… More

From US$ 865 Book Now

Hi Country Haus Unit 1805

126 Hi Country Dr #1805, Winter Park, United States Show map

Offering a Jacuzzi for a relaxing experience, Hi Country Haus Unit 1805 Villa Winter Park is located a 10-minute drive from the outdoor sports store "Colorado Adventure Park". Providing guests with… More

From US$ 424 Book Now

Stunning Winter Park Condo Near Slopes!

400 Baker Dr, Winter Park, United States Show map

Situated within 5 minutes' walk of Cozens Ranch House Museum, the 3-bedroom Stunning Winter Park Condo Near Slopes! villa is ideal for up to 8 guests. Featuring a Jacuzzi, this welcoming holiday home… More

From US$ 855 Book Now

Walkable Winter Park Condo ~ 4 Mi To Slopes!

79114 Us-40 Unit B-32, Winter Park, United States Show map

Located around 5 minutes' walk from Cooper Creek Square, the 3-bedroom Walkable Winter Park Condo ~ 4 Mi To Slopes! villa gives easy access to various tourist attractions in the area. Featuring a… More

From US$ 352 Book Now

Leland Creek Home

Winter Park, United States Show map

The 5-bedroom Leland Creek Home Winter Park is located 4.8 km from Winter Park Resort and provides hiking for active guests. With a maximum capacity of 13 guests, the villa offers parking. More

From US$ 936 Book Now

Downtown Wp Villa 262 I Arcade I Private Rooftop Hot Tub With Views I Discounted Attractions

262 Lionsgate Dr., Winter Park, United States Show map

Located a few steps from Vasquez Peak Wilderness, the 4-bedroom Downtown Wp Villa 262 I Arcade I Private Rooftop Hot Tub With Views I Discounted Attractions Winter Park offers quick access to various… More

From US$ 583 Book Now

12 Yukon Lane Townhome

Winter Park, United States Show map

During the stay at 12 Yukon Lane Townhome Winter Park villa, guests can indulge in a Jacuzzi or visit Cozens Ranch House Museum, located 25 minutes' walk away. Located 3.3 km from Olympia Express… More

From US$ 1109 Book Now

Vasquez Vista

500 Vasquez Rd, 1, Winter Park, United States Show map

Featuring horse riding tours to make your visit more entertaining, the 2-bedroom Vasquez Vista Villa Winter Park is 3.2 km from Eskimo Express. Guests can enjoy snow skiing, hiking, and horseback… More

From US$ 427 Book Now

100 Steps To Gondola: Cozy Winter Park Condo!

670 Winter Park Dr Unit 3514, Winter Park, United States Show map

Offering a Jacuzzi for guests to unwind, the 2-bedroom 100 Steps To Gondola: Cozy Winter Park Condo! villa is located a stone's throw from Main Street. This Winter Park holiday home features… More

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Trailside Mountain Retreat With Private Hot Tub

395 Arapahoe Road Winter Park, Co 80482, Winter Park, United States Show map

Offering access to entertainment venues such as Winter Park Resort, situated nearly a 10-minute drive away, the 4-bedroom Trailside Mountain Retreat With Private Hot Tub Villa Winter Park can host up… More

From US$ 592 Book Now

Fraser Crossing 3518 Studio

670 Winter Park Dr #3518, Winter Park, United States Show map

The spacious 41 m² Fraser Crossing 3518 Studio Winter Park is located in Winter Park, within a 3-km distance of Pioneer Express, and pampers guests with a hot tub. The apartment has a convenient… More

From US$ 289 Book Now

Ski In Out Chalet 277 I Hot Tub I Theatre I Views I Game Room I Bunk Room I Discounted Attractions

277 Bridger Trail, Winter Park, United States Show map

Located only 7 minutes' walk from Iron Horse Lift, the 4-bedroom Alpine Luxury Chalet: Ski-In/Out with Hot Tub & Activities Winter Park offers a games room for guests' entertainment. More

From US$ 4406 Book Now

Beaver Village Unit #0724

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

The spacious 2-bedroom Beaver Village Unit #0724 Winter Park apartment is located 3.8 km from the outdoor sports store "Colorado Adventure Park" and approximately 10 minutes by car from Gemini… More

From US$ 276 Book Now

Downtown Wp Condo 1409 I Hot Tub I Ac I Great Views I Activity Program

144 Ski Idlewild Rd. #1409, Winter Park, United States Show map

The 2-bedroom Downtown Wp Condo 1409 I Hot Tub I Ac I Great Views I Activity Program Winter Park villa is situated a mere 5 minutes on foot from Cooper Creek Square, featuring such comforts as Wi-Fi… More

From US$ 394 Book Now

Beaver Village Unit #0712R

193 Gcr 702 #3-102 Or 193 Village Dr #3-102, Winter Park, United States Show map

Situated 3.2 km from Pioneer Express, the 58 m² Beaver Village Unit #0712R Winter Park apartment can host up to 4 guests in Winter Park. This 1-bedroom apartment boasts a Jacuzzi and a sauna offering… More

From US$ 203 Book Now

Downtown Wp Loft 206 I Huge Hot Tub I Great Views I Activity Program

400 Baker Drive #206, Winter Park, United States Show map

Situated a 5-minute walk from The Foundry Cinema and Bowl, Luxury Loft 206: Hot Tub Retreat with Mountain Views Villa Winter Park entices guests with views of the mountain. Suitable for up to 10… More

From US$ 522 Book Now

Downtown Wp Loft 307 I Huge Hot Tub I Great Views I Heated Garage I Discounted Attractions

400 Baker Dr. #307, Winter Park, United States Show map

Up to 6 guests can stay at the 2-bedroom Luxury Loft 307: Mountain Views & Hot Tub Retreat Villa Winter Park and enjoy The Foundry Cinema and Bowl, located nearly 5 minutes' walk away. This holiday… More

From US$ 365 Book Now

Hi Country Haus 6-15

471 High Country Dr, Building 6, Unit 15, Winter Park, United States Show map

The 46 m² Hi Country Haus 6-15 Apartment Winter Park is located in Winter Park, 2.5 km from Fraser Tubing Hill, and pampers guests with a Jacuzzi. A range of activities, such as snow skiing… More

From US$ 68 Book Now

Winter Park Condo W/ Sleeping Loft - Near Main St

145 Arapahoe Rd Unit 203, Winter Park, United States Show map

The welcoming Winter Park Condo W/ Sleeping Loft - Near Main St villa is located 3.5 km from Main Street and welcomes its guests to enjoy hiking. Offering balloon rides, this 2-bedroom holiday home… More

From US$ 207 Book Now

The Red Fox | Condo Near Ski Shuttle | Studio 40

U.S. 40 E-307, Winter Park, United States Show map

The Red Fox Studio 40 Location Winter Park overlooks the garden and is situated merely a 5-minute walk from Be.. Boutique. 3.2 km from Pioneer Express, this apartment comes with a fitness suite and a… More

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Downtown Wp Condo 2203 I Hot Tub I Ac I Views I Gas Firepit I Office I Discounted Attractions

144 Ski Idlewild Rd #2203, Winter Park, United States Show map

Luxury Condo 2203: Hot Tub & Views with Activity Perks Winter Park villa provides an opportunity to stay within 300 metres of Cooper Creek Square and offers a Jacuzzi, perfect for decompressing. The… More

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Downtown Wp Villa 305 I Private Hot Tub I Views I Bunk Room I Discounted Attractions

305 Red Quill Way, Winter Park, United States Show map

Luxury Villa 305: Private Hot Tub & Scenic Views Winter Park enjoys a prime location, 12 minutes' walk from Cooper Creek Square, and offers guests to unwind in a Jacuzzi. Offering balloon tours, the… More

From US$ 927 Book Now

Beautiful 2 Bedroom, Vaulted Ceilings, 3 Bathrooms, Private Hot Tub, Winter Park Colorado

151 Telemark Dr B-1 U-15 Winter Park, Winter Park, United States Show map

Staying at Beautiful 2 Bedroom, Vaulted Ceilings, 3 Bathrooms, Private Hot Tub, Winter Park Colorado villa, guests can easily reach Cozens Ranch House Museum, located only 400 metres away. More

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Cozy Corner

490 Kings Crossing Rd Apt 331, Winter Park, United States Show map

The 64 m² Cozy Corner Apartment Winter Park is located in Winter Park, about 4 km from Main Street, and boasts a Jacuzzi and an indoor pool. The maximum occupancy at this 2-bedroom apartment is 6… More

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Wp Resort Ski In Out Condo 1221 I Hot Tub I Gym I Ski Views I Discounted Attractions

201 Zephyr Mountain Way #1221, Winter Park, United States Show map

Located about a 5-minute walk from Winter Park Resort, the 2-bedroom Ski-In/Ski-Out Luxury Condo: Mountain Views & Hot Tub Retreat Winter Park villa offers a Jacuzzi for additional relaxation. More

From US$ 339 Book Now

3 Mi To Winter Park Resort: Mtn-View Haven!

720 Baker Dr Unit 405, Winter Park, United States Show map

The 3-bedroom 3 Mi To Winter Park Resort: Mtn-View Haven! villa hosts up to 10 guests and provides proximity to Cozens Ranch House Museum, situated nearly a 5-minute stroll away. Providing guests… More

From US$ 424 Book Now

Walk To Shops & Dining! Winter Park Condo W/ Pool

50 Village Dr Unit 434, Winter Park, United States Show map

Positioned 4 km from bustling shopping destinations such as the outdoor sports store "Colorado Adventure Park", Walk To Shops & Dining! Winter Park Condo W/ Pool villa offers guests to use private… More

From US$ 469 Book Now

Fresh Tracks At Peak View Ridge

38 Wheeler Road, Winter Park, United States Show map

The 4-bedroom Fresh Tracks At Peak View Ridge Villa Winter Park is situated approximately 5 minutes on foot from Ski Idlewild Abondoned Chairlift, featuring such comforts as Wi-Fi and parking. The… More

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Beautiful Fraser Crossing Founders Pointe Condo With Upgraded Furnishings Condo

201 Zephyr Way, Winter Park, United States Show map

Situated a 14-minute walk from Alpine Slide, Beautiful Fraser Crossing Founders Pointe Condo With Upgraded Furnishings Condo Winter Park offers a hot tub for 6 visitors. At this apartment, Wi-Fi and… More

From US$ 736 Book Now

Dine, Shop & Shuttle To Resort: Winter Park Haven!

518 Hi Country Dr Unit 13-14, Winter Park, United States Show map

During the stay at the 3-bedroom Dine, Shop & Shuttle To Resort: Winter Park Haven! villa, guests can indulge in a Jacuzzi and an indoor pool or visit Cozens Ranch House Museum, located around 25… More

From US$ 188 Book Now

Beaver Village Unit #0332

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

The 1-bedroom Beaver Village Unit #0332 Winter Park apartment is within 3 km of Discovery. About a 10-minute ride from Main Street, the apartment includes a heated pool as well as a Jacuzzi and a… More

From US$ 567 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 about 15 minutes' walk from Winter Park Jazz Festival. Boasting a hot tub, this 1-bedroom apartment, suitable for 3 guests, is 3.3 km from… More

From US$ 185 Book Now

Iron Horse Resort D3084

310 Iron Horse Way, Building D, Unit #3084, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the spacious 1-bedroom Iron Horse Resort D3084 Winter Park, which is approximately 25 minutes' walk from High Lonesome Express and a mere 1.1 km from… More

From US$ 209 Book Now

Condo W/ Mountain Views In Heart Of Downtown!

144 Ski Idlewild Rd Unit 2407, Winter Park, United States Show map

The 3-bedroom Condo W/ Mountain Views In Heart Of Downtown! Winter Park villa is located merely 6 minutes' stroll from Cooper Creek Square and offers a Jacuzzi for guests' relaxation. Offering Wi-Fi,… More

From US$ 969 Book Now

Downtown Winter Park Condo W/ Free Bus To Ski Base

78491 Us-40 Unit 3, Winter Park, United States Show map

Positioned 10 minutes' drive from bustling shopping destinations such as the outdoor sports store "Colorado Adventure Park", Downtown Winter Park Condo W/ Free Bus To Ski Base villa offers guests to… More

From US$ 171 Book Now

Winter Park Condo Rental: 4 Mi To Ski Resort!

Crestview 79050 Us-40 Unit D609, Winter Park, United States Show map

Positioned 3.8 km from bustling shopping destinations such as the outdoor sports store "Colorado Adventure Park", Winter Park Condo Rental: 4 Mi To Ski Resort! villa offers guests to use private… More

From US$ 258 Book Now

Downtown Winter Park Condo: Steps To Everything!

144 Ski Idlewild Rd Building B, Unit 2409, Winter Park, United States Show map

Offering a Jacuzzi for a relaxing experience, the 1-bedroom Downtown Winter Park Condo: Steps To Everything! villa is located 3.8 km from the outdoor sports store "Colorado Adventure Park". More

From US$ 316 Book Now

New Luxury Timber Fox 3301

144 Ski Idlewild Road 3301, Winter Park, United States Show map

The 101 m² New Luxury Timber Fox 3301 Apartment Winter Park is located 3.5 km from Endeavour Lift and only a 5-minute walk from Cooper Creek Square. Boasting a location a few steps from Vasquez Peak… More

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Ski In Out Condo 3325 I Huge Hot Tub I Great Views I Heated Garage I Discounted Attractions

670 Winter Park Dr. #3325, Winter Park, United States Show map

The 2-bedroom Ski-In/Out Luxury Condo: Mountain Views & Hot Tub Retreat Winter Park villa entices guests to enjoy snow skiing and mini golf and offers proximity to Winter Park Resort, located only… More

From US$ 332 Book Now

Silverado II Unit 334

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

Situated about 10 minutes' drive from Fraser Tubing Hill, the spacious 2-bedroom Silverado II Unit 334 Winter Park apartment can host up to 6 guests in Winter Park. The apartment boasts access to a… More

From US$ 345 Book Now

Fraser Crossing Founders Pointe, Studio Apartment Premium Unit 3620

1610 Carolina Beach Ave. N Unit A12, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 1-bedroom Fraser Crossing Founders Pointe, Studio Apartment Premium Unit 3620 Winter Park, which is 2.8 km from Prospector Express and a mere 13… More

From US$ 398 Book Now

Idyllic Condo ~ 5 Mi To Winter Park Resort!

126 High Country Dr Unit 6, Winter Park, United States Show map

During the stay at Idyllic Condo ~ 5 Mi To Winter Park Resort! villa, guests can indulge in a Jacuzzi and an indoor pool or visit the outdoor sports store "Colorado Adventure Park", located… More

From US$ 631 Book Now

Beaver Village Unit #0621

195 Gcr 702 #2-201 Or 195 Village Dr #2-201, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the spacious 79 m² Beaver Village Unit #0621 Winter Park apartment, which is 3.8 km from the outdoor sports store "Colorado Adventure Park" and just 12… More

From US$ 345 Book Now

Hi Country Haus Unit 1009

432 Hi Country Dr #1009, Winter Park, United States Show map

The spacious 46 m² Hi Country Haus Unit 1009 Apartment Winter Park is situated in Winter Park, only 1.4 km from Saint Bernard Of Montjoux, and offers spa amenities such as a Jacuzzi. Approximately a… More

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Hi Country Haus Unit 2501

426 Hi Country Dr #2501, Winter Park, United States Show map

The 66 m² Hi Country Haus Unit 2501 Apartment Winter Park is located 9 minutes on foot from The Foundry Cinema and Bowl and 4.7 km from Pioneer Express. Providing a Jacuzzi, this 1-bedroom apartment… More

From US$ 505 Book Now

Ski-In/Ski-Out Studio At Winter Park Base!

101 Iron Horse Way Unit C1043, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the family-friendly 1-bedroom Ski-In/Ski-Out Studio At Winter Park Base!, which is merely 14 minutes' walk from Winter Park Resort and a mere 0.9 km… More

From US$ 182 Book Now

Winter Park Resort Villa 509 I Private Hot Tub I Great Views I Discounted Attractions

509 Antler Way, Winter Park, United States Show map

Located only 600 metres from Main Street, the 3-bedroom Luxury Villa Retreat: Hot Tub, Views & Complimentary Activities Winter Park can accommodate up to 12 guests, providing them with a hot tub for… More

From US$ 2130 Book Now

Winter Park Condo W/ Private Balcony: Near Skiing!

480 Hi Country Dr Unit 24-8, Winter Park, United States Show map

The Foundry Cinema and Bowl is 5 minutes' walk from the welcoming Winter Park Condo W/ Private Balcony: Near Skiing! villa, offering a hot tub for guests' relaxation. Providing guests with Wi-Fi and… More

From US$ 604 Book Now

Downtown Wp Villa 254 I Private Rooftop Hot Tub I Great Views I Arcade I Discounted Attractions

254 Lions Gate Dr., Winter Park, United States Show map

During the stay at Downtown Wp Villa 254 I Private Rooftop Hot Tub I Great Views I Arcade I Discounted Attractions Winter Park, guests can indulge in a Jacuzzi or visit the outdoor sports store… More

From US$ 350 Book Now