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2026-11-14
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Vacation Rentals in Winter Park

Downtown Wp River Front Villa 244 I Private Hot Tub I Views I Game Room I Discounted Attractions

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

The 5-bedroom Riverside Luxury Villa: Hot Tub, Views & Free Activities Winter Park is situated around 5 minutes' walk from Cooper Creek Square and offers guests to relax with a hot tub. At the… More

From US$ 1876 Book Now

Beaver Village Unit #0211

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

The 2-bedroom Beaver Village Unit #0211 Winter Park apartment is a mere 9 minutes' walk from Be.. Boutique. Boasting a Jacuzzi and a sauna, this spacious apartment, suitable for 6 guests, is 4.8 km… More

From US$ 448 Book Now

Downtown Wp Penthouse Condo 304 I Great Views I Activity Program

377 Lions Gate Dr. #304, Winter Park, United States Show map

During the stay at the 3-bedroom Luxury Penthouse #304: Panoramic Views & Complimentary Activities Villa Winter Park, guests can indulge in snow skiing and mini golf or visit Fraser Tubing Hill… More

From US$ 550 Book Now

Hi Country Haus Unit 0309

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

To enjoy your vacation in Winter Park, stay at the spacious 48 m² Hi Country Haus Unit 0309 Apartment Winter Park, which is around a 10-minute ride from the outdoor sports store "Colorado Adventure… More

From US$ 540 Book Now

2 Mi To Winter Park Resort: Condo W/ Pool Access!

79114 U.S. Hwy 40 Unit B22, Winter Park, United States Show map

The 2-bedroom 2 Mi To Winter Park Resort: Condo W/ Pool Access! villa provides easy access to various city attractions, such as Hideaway Park, situated nearly 5 minutes' walk away. Suitable for 7… More

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Iron Horse Building C Unit 1023

Winter Park, United States Show map

The 52 m² Iron Horse Building C Unit 1023 Apartment Winter Park is located in Winter Park, 1 km from Winter Park Resort, and pampers guests with a Jacuzzi. Also, there is an outdoor swimming pool to… More

From US$ 237 Book Now

Snowblaze Condos Building C Unit 24

Winter Park, United States Show map

The spacious Snowblaze Condos Building C Unit 24 Winter Park is located in Winter Park, 4.3 km from Prospector Express, and boasts a hot tub and a sauna. Guests can use Wi-Fi for either business or… More

From US$ 476 Book Now

Downtown Wp Condo 1209 I Hot Tub I Ac I Great Views I Activity Program

144 Ski Idlewild Rd #1209, Winter Park, United States Show map

Situated a 5-minute walk from Hideaway Park, Luxury Skyhigh Condo: Hot Tub, Views & Activity Perks Winter Park villa entices guests with views of the mountain. The 2-bedroom holiday home features… More

From US$ 325 Book Now

Winter Park Resort Villa 607 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions

607 Trailside Lane, Winter Park, United States Show map

Located approximately a 25-minute walk from Looking Glass, the 3-bedroom Luxury Villa Retreat: Hot Tub, Views & Activity Package Winter Park entices guests to relax in a Jacuzzi. Featuring fitness… More

From US$ 282 Book Now

Hi Country Haus Haven

382 High Country Dr Bldg 3, Unit 15, Winter Park, United States Show map

Hi Country Haus Haven Apartment Winter Park is situated in Winter Park, 12 minutes' walk from Cozens Ranch House Museum, and offers spa amenities such as a Jacuzzi. Also, there is a swimming pool to… More

From US$ 165 Book Now

Hi Country Haus Getaway

382 Hi Country Drive, Building 3, Unit 10, Winter Park, United States Show map

The 43 m² Hi Country Haus Getaway Apartment Winter Park is located approximately 10 minutes' drive from the outdoor sports store "Colorado Adventure Park" and approximately 5 km from Winter Park… More

From US$ 112 Book Now

Downtown Wp Villa 268 I Private Rooftop Hot Tub I Great Views I Bunk Room I Discounted Attractions

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

The 4-bedroom Downtown Wp Villa 268 I Private Rooftop Hot Tub I Great Views I Bunk Room I Discounted Attractions Winter Park is situated just 5 minutes' walk from Vasquez Peak Wilderness, featuring… More

From US$ 669 Book Now

Zephyr Mountain Lodge, Condo - 2 Bedroom Select-Rated Condo 2203

201 Zephyr Way, Winter Park, United States Show map

Zephyr Mountain Lodge, Condo - 2 Bedroom Select-Rated Condo 2203 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$ 356 Book Now

Condo On Fraser River < 4 Mi To Winter Park Resort

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

Located approximately a 20-minute walk from Idlewild Distillery, the welcoming Condo On Fraser River 4 Mi To Winter Park Resort villa gives access to various tourist sites in the vicinity. This 2… More

From US$ 160 Book Now

Beaver Village Unit #0131

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

To enjoy your vacation in Winter Park, stay at the spacious 92 m² Beaver Village Unit #0131 Winter Park apartment, which is around a 10-minute ride from Endeavour Lift and approximately 700 metres… More

From US$ 774 Book Now

4Br Winter Park Oasis - Sleeps 9 - Ski-In And Hot Tub

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

The spacious 1-bedroom 4Br Winter Park Oasis - Sleeps 9 - Ski-In And Hot Tub apartment is just 0.6 km from Idlewild Distillery. The apartment can host up to 9 guests. More

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Beaver Village Unit #0232R

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

The spacious 60 m² Beaver Village Unit #0232R Winter Park apartment is situated in Winter Park, only 650 metres from Hideaway Park, and offers spa amenities such as a Jacuzzi and a sauna. Fraser… More

From US$ 350 Book Now

Cozy Ski-In/Ski-Out Winter Park Resort Condo!

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

The 1-bedroom Cozy Ski-In/Ski-Out Winter Park Resort Condo! villa is nestled approximately 5 minutes' walk from Winter Park Resort and can accommodate up to 4 guests. Boasting spa therapy, a terrace,… More

From US$ 202 Book Now

Downtown Wp Condo 2307 I Hot Tub I Ac I Great Views I Activity Program

144 Ski Idlewild Rd. #2307, Winter Park, United States Show map

The 2-bedroom Downtown Wp Condo 2307 I Hot Tub I Ac I Great Views I Activity Program Winter Park villa is located about a 10-minute drive from the outdoor sports store "Colorado Adventure Park" and… More

From US$ 443 Book Now

Beaver Village 1712 - Nicely Updated, 2 Queens Plus 2 Twins, Pool, Hot Tubs, Sauna

216 Village Drive, #17-12, Winter Park, United States Show map

Beaver Village 1712 - Nicely Updated, 2 Queens Plus 2 Twins, Pool, Hot Tubs, Sauna Winter Park apartment is located 3.2 km from Gemini Express and 25 minutes' walk from Cozens Ranch House Museum. Wi… More

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Winter Park Condo W/ Resort Shuttle On-Site!

201 Gcr 702 Unit 10-202, Winter Park, United States Show map

Featuring an outdoor swimming pool, the welcoming Winter Park Condo W/ Resort Shuttle On-Site! villa is suitable for up to 8 people and is located 3.3 km from Main Street. Providing guests with Wi-Fi… More

From US$ 431 Book Now

Downtown Wp River Front Villa 242 I Private Hot Tub I Great Views I Activity Program

242 Lions Gate Drive, Winter Park, United States Show map

During the stay at Riverside Luxury Villa: Hot Tub Views & Activity Perks Winter Park, guests can indulge in a hot tub or visit the outdoor sports store "Colorado Adventure Park", located 3.4 km away… More

From US$ 718 Book Now

Zephyr Mountain Lodge Premium-Rated 1214

201 Zephyr Way, Winter Park, United States Show map

The 1-bedroom Zephyr Mountain Lodge Premium-Rated 1214 Winter Park is just 5 minutes' stroll from Winter Park Resort and welcomes guests with a Jacuzzi. Discovery is 2.6 km from the apartment while… More

From US$ 697 Book Now

Fraser Crossing Top Floor 3603

670 Winter Park Dr Unit 3603, Winter Park, Co 80482, Winter Park, United States Show map

At the 1-bedroom Fraser Crossing Top Floor 3603 Winter Park villa, guests can enjoy snow skiing, hiking, and cycling as well as a location nearly 5 minutes' walk from Winter Park Resort. Featuring a… More

From US$ 203 Book Now

Downtown Wp Condo 2208 I Private Hot Tub I Ac I Great Views I Activity Program

144 Ski Idlewild Rd. Unit 2208, Winter Park, United States Show map

During the stay at the 3-bedroom Luxury Condo 2208: Hot Tub, AC & Views with Activity Perks Winter Park villa, guests can indulge in a Jacuzzi or visit Cozens Ranch House Museum, located around 20… More

From US$ 268 Book Now

Ski In Out Luxury Condo 2207 Hot Tub Gym Ski Views Best Price 500 Dollars In Free Activities Daily

201 Zephyr Way #2207, Winter Park, United States Show map

The 2-bedroom Ski In Out Luxury Condo 2207 Hot Tub Gym Ski Views Best Price 500 Dollars In Free Activities Daily Winter Park villa is situated approximately a 5-minute walk from Moffat Tunnel… More

From US$ 349 Book Now

Winter Park Condo With Fireplace And Mountain Views

100 Hideaway Dr, Winter Park, Co 80482, Usa, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 50 m² Winter Park Condo With Fireplace And Mountain Views, which is about 10 minutes' drive from Prospector Express and 3.8 km from Main Street. More

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Arrow At Winter Park Unit 202

78710 Us Highway 40, Winter Park, United States Show map

Located 3.3 km from the outdoor sports store "Colorado Adventure Park", the 112 m² Arrow At Winter Park Unit 202 Apartment overlooks the mountain. The spacious apartment capacity is based on up to 6… More

From US$ 476 Book Now

Condo In The Heart Of Dtwn Winter Park

801 Trailhead Cir Unit 813, Winter Park, United States Show map

Situated approximately 5 minutes' walk from Winter Park Jazz Festival, 3-bedroom Condo In The Heart Of Dtwn Winter Park villa offers quick access to numerous city landmarks nearby. Featuring a… More

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Ski-In Ski-Out Zephyr 1 Bedroom Condo 2204

201 Zephyr Way 2Nd, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 53 m² Ski-In Ski-Out Zephyr 1 Bedroom Condo 2204 Winter Park, which is merely 0.9 km from Coca Cola Tubing Hill At Winter Park and only a 14-minute… More

From US$ 217 Book Now

Ski In Out Condo 4283 I Huge Hot Tub I Great Views I Heated Garage I Discounted Attractions

580 Winter Park Dr., Winter Park, United States Show map

Located within 5 minutes' walk of Zephyr Express, the 2-bedroom Ski-In/Out Luxury Condo: Mountain Views & Hot Tub Retreat Winter Park villa offers fitness classes, as well as a fitness room for… More

From US$ 273 Book Now

Slopeside Villa 126 I Ski Views I Private Hot Tub I Bunks I Steam Shower I Discounted Attractions

126 Cedar Drive, Winter Park, United States Show map

Situated within 10 minutes' walk of Main Street, the 3-bedroom Slopeside Luxury Villa: Resort-Adjacent with Steam Shower & Activity Perks Winter Park entices guests with snow skiing and mini golf in… More

From US$ 652 Book Now

Downtown Wp Villa 307 I Private Hot Tub I Views I Bunk Room I Desk I Discounted Attractions

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

During the stay at the 4-bedroom Luxury Villa 307: Private Hot Tub & Scenic Views Winter Park, guests can indulge in snow skiing and mini golf or visit Cozens Ranch House Museum, located 1.3 km away.… More

From US$ 381 Book Now

Ski In Out Loft 102 I Hot Tub I Gym I Great Views I Activity Program

422 Iron Horse Way #102, Winter Park, United States Show map

During the stay at Ski In Out Loft 102 I Hot Tub I Gym I Great Views I Activity Program Winter Park villa, guests can indulge in snow skiing and mini golf or visit Winter Park Resort, located 14… More

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Winter Park Condo On Bus Route, 2 Blocks To Dtwn!

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

Nestled 4.8 km from Main Street, the welcoming Winter Park Condo On Bus Route, 2 Blocks To Dtwn! villa is boasting a patio and playground for guests' enjoyment. Located approximately 10 minutes by… More

From US$ 153 Book Now

Winter Park Condo W/ Hot Tub, Balcony & Shuttle!

144 Ski Idlewild Rd Unit 2308, Winter Park, United States Show map

The welcoming Winter Park Condo W/ Hot Tub, Balcony & Shuttle! villa, located merely 5 minutes' walk from Cooper Creek Square, can host up to 9 guests. Offering a Jacuzzi, this 3-bedroom holiday home… More

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Cozy Ski-In/Ski-Out Winter Park Resort Condo!

313 Iron Horse Way Unit C1053, Winter Park, United States Show map

Situated just 11 minutes' walk from Cabriolet, the spacious 1-bedroom Cozy Ski-In/Ski-Out Winter Park Resort Condo! can host up to 2 guests in Winter Park. Wi-Fi and private car parking are also… More

From US$ 268 Book Now

Downtown Wp Penthouse P2 With Spectacular Views I Activity Program

147 Forest Trail P2, Winter Park, United States Show map

Located approximately a 15-minute walk from Hideaway Park, the 3-bedroom Luxury Penthouse: Spectacular Views & Activity Perks Villa Winter Park entices guests to relax in a hot tub. Featuring fitness… More

From US$ 476 Book Now

Hi Country Haus Unit 2110

51 River Drive, Winter Park, United States Show map

Offering spa facilities such as a Jacuzzi, the spacious 2-bedroom Hi Country Haus Unit 2110 Apartment Winter Park is situated just 0.9 km from Saint Bernard of Montjoux Catholic Church. The 119 m²… More

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Crestview Place Unit 607

79050 Us Hwy 40 #D-607, Winter Park, United States Show map

Situated about a 10-minute drive from Discovery, the spacious 135 m² Crestview Place Unit 607 Winter Park apartment offers a Jacuzzi for 8 visitors. Prospector Express is 3.3 km from the 3-bedroom… More

From US$ 446 Book Now

Winter Park Condo W/ Fireplace - 4 Mi To Slopes!

Winter Park, United States Show map

Winter Park Condo W/ Fireplace - 4 Mi To Slopes! villa, located nearly a 5-minute walk from The Foundry Cinema and Bowl, can host up to 7 guests. Featuring a Jacuzzi, this 2-bedroom welcoming holiday… More

From US$ 802 Book Now

Ski-In/Ski-Out Winter Park Condo At Iron Horse

313 Iron Horse Way Unit C3113, Winter Park, United States Show map

Located just a 13-minute walk from Zephyr Express, the 2-bedroom Ski-In/Ski-Out Winter Park Condo W/ Mountain Views villa entices guests to relax in a hot tub. Offering balloon rides, this property… More

From US$ 355 Book Now

Ski In Out Luxury Condo 2403 Hot Tub Gym Ski Views Best Price 500 Dollars Free Activities Daily

201 Zephyr Way #2403, Winter Park, United States Show map

The 2-bedroom Ski In Out Luxury Condo 2403 Hot Tub Gym Ski Views Best Price 500 Dollars Free Activities Daily Winter Park villa entices guests to enjoy snow skiing and mini golf and offers proximity… More

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Timber Lake 341

Winter Park, United States Show map

Situated 3.4 km from the outdoor sports store "Colorado Adventure Park", the 3-bedroom Timber Lake 341 Winter Park villa entices guests to explore various tourist attractions in the area. Guests can… More

From US$ 1110 Book Now

Mountain View Retreat, Walk To Winter Park Gondola

Winter Park, United States Show map

Offering a hot tub, the 3-bedroom Mountain View Retreat, Walk To Winter Park Gondola Villa is located around a 10-minute walk from Prospector Express. Suitable for up to 8 guests, this property… More

From US$ 985 Book Now

Beaver Village Unit #0521R

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

Situated a 12-minute walk from Be.. Boutique, Beaver Village Unit #0521R Winter Park apartment offers a Jacuzzi and a sauna for 4 visitors. Wi-Fi is available for guests' business or leisure needs. More

From US$ 234 Book Now

Ski In Out Village Condo 4454 I Huge Hot Tub I Views I Heated Garage I Discounted Attractions

580 Winter Park Dr. #4454, Winter Park, United States Show map

Located about a 5-minute walk from Winter Park Resort, the 2-bedroom Ski-View Luxury Condo: Hot Tub & Activity Perks Winter Park villa offers a hot tub for additional relaxation. Featuring fitness… More

From US$ 418 Book Now

Downtown Wp Villa 558 I Great Views I Private Hot Tub I Discounted Attractions

558 Baker Dr., Winter Park, United States Show map

Located only a 9-minute walk from Cozens Ranch House Museum, the 2-bedroom Luxury Pond Villa: Hot Tub & Views with Complimentary Activities Winter Park offers a hot tub for additional relaxation. More

From US$ 201 Book Now

Winter Park Resort Villa 502 I Private Hot Tub I Great Views I Bunk Rooms I Discounted Attractions

502 Reserve Way, Winter Park, United States Show map

Situated only a 9-minute walk from Main Street, the 3-bedroom Winter Park Resort Villa 502 I Private Hot Tub I Great Views I Bunk Rooms I Discounted Attractions offers a Jacuzzi and can accommodate… More

From US$ 575 Book Now

Iron Horse Building D Unit 4104

Winter Park, United States Show map

The 1-bedroom Iron Horse Building D Unit 4104 Apartment Winter Park is situated in Winter Park, nearly 25 minutes on foot from Rollins Pass, and offers spa amenities such as a Jacuzzi. Winter Park… More

From US$ 258 Book Now