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2026-11-03
2026-11-04
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Holiday Homes in Winter Park

Winter Park Resort Home 960 I Private Hot Tub I Great Views I Game Room I Discounted Attractions

960 Arrow Trail, Winter Park, United States Show map

The 4-bedroom Custom Luxury Villa: Resort-Adjacent with Hot Tub and Activity Perks Winter Park is located merely 1.4 km from Winter Park Resort and allows guests to enjoy snow skiing and mini golf. More

From US$ 910 Book Now

Unwind Poolside, Walk To Main St! Winter Park Stay

301 Lions Gate Dr Unit 119, Winter Park, United States Show map

Situated merely 1.3 km from Cozens Ranch House Museum, the 2-bedroom Unwind Poolside, Walk To Main St! Winter Park Stay villa offers guests to enjoy a terrace and entertainment facilities. Offering a… More

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Downtown Wp River Villa 582 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions

582 Telemark Ct., Winter Park, United States Show map

Boasting a Jacuzzi, the 3-bedroom Downtown Wp River Villa 582 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions Winter Park is located merely 5 minutes' walk from Cozens Ranch… More

From US$ 363 Book Now

Luxury Mountain Retreat

300 North Woods Place, Winter Park, United States Show map

Offering a Jacuzzi and a sauna for a relaxing experience, Luxury Mountain Retreat Villa Winter Park is located 20 minutes' walk from Winter Park Resort. Providing guests with high-speed Internet… More

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Winter Park Resort Villa 160 I Private Hot Tub I Great Views I Game Room I Activity Program

160 Dreamcatcher South, Winter Park, United States Show map

Situated merely 7 minutes' walk from Main Street, the 5-bedroom Winter Park Resort Villa 160 I Private Hot Tub I Great Views I Game Room I Activity Program offers a Jacuzzi and a sauna and can… More

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Arcade Ski-In Ski-Out Retro Camp Vibes Treecondo

100 Iron Horse Way, Winter Park, United States Show map

The 2-bedroom Arcade Ski-In Ski-Out Retro Camp Vibes Treecondo Winter Park villa hosts up to 7 guests and provides proximity to Coca Cola Tubing Hill At Winter Park, situated a mere 0.8 km away. More

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3 Mi To Slopes! Family-Friendly Winter Park Escape

225 Hi Country Dr Unit 5-613, Winter Park, United States Show map

Offering access to entertainment venues such as The Foundry Cinema and Bowl, situated just 0.6 km away, the 2-bedroom 3 Mi To Slopes! Family-Friendly Winter Park Escape Villa can host up to 6 guests.… More

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New Headwaters Condo 209 I Great Views I Best Price I Free Adventures Daily

720 Baker Dr. #209, Winter Park, United States Show map

The 2-bedroom New Headwaters Condo 209 I Great Views I Best Price I Free Adventures Daily Winter Park villa offers easy access to such tourist spots as The Foundry Cinema and Bowl, located only a 5… More

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Founders Pointe-Winter Park Base-Massive Hot Tub

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

Situated approximately 7 km from Mary Jane Base, Founders Pointe-Winter Park Base-Massive Hot Tub villa provides access to numerous tourist attractions in the area. More

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Cozy Winter Park Condo W/ Hot Tub & Shuttle!

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

Offering a Jacuzzi and a sauna for a relaxing experience, the welcoming Cozy Winter Park Condo W/ Hot Tub & Shuttle! villa is located a 10-minute ride from Cozens Ranch House Museum. The 2-bedroom… More

From US$ 292 Book Now

Easy Ski Shuttle Access! Winter Park Mtn Getaway

490 Kings Crossing Rd Unit 611, Winter Park, United States Show map

Featuring a heated pool, Easy Ski Shuttle Access! Winter Park Mtn Getaway villa is suitable for up to 6 people and is located within a 10-minute drive of Main Street. Providing guests with Wi-Fi and… More

From US$ 291 Book Now

Downtown Wp Timber Top Home I Hot Tub I Views I Game Room I Bunks I Discounted Attractions

29 Timber Circle, Winter Park, United States Show map

Offering a Jacuzzi for a relaxing experience, Timber Top Villa: Luxury Retreat with Hot Tub and Stunning Views Winter Park is located 4 km from Coca Cola Tubing Hill At Winter Park. Providing guests… More

From US$ 732 Book Now

Downtown Wp Condo 102 I Great Views I Arcade Games I Activity Program

377 Lions Gate Dr. #102, Winter Park, United States Show map

The 1-bedroom Luxury Condo 102: Panoramic Views & Activity Perks Winter Park villa offers easy access to such tourist spots as Vasquez Peak Wilderness, located only a 5-minute walk away. More

From US$ 418 Book Now

Ski & Hike! Easy Adventuring At Winter Park Condo

301 Lions Gate Dr Unit 102, Winter Park, United States Show map

Up to 8 guests can stay at the 3-bedroom Ski & Hike! Easy Adventuring At Winter Park Condo villa and enjoy Vasquez Peak Wilderness, located approximately a 5-minute walk away. Offering a Jacuzzi, the… More

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Short Walk To Ski Trail Or Shuttle To Wp Village

496 Iron Horse Way, Winter Park, United States Show map

The 4-bedroom Short Walk To Ski Trail Or Shuttle To Wp Village Winter Park villa is located merely 1.2 km from Winter Park Resort and provides snow skiing and hiking for active guests. Offering a hot… More

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Downtown Wp Chalet 100 I Private Hot Tub I Great Views I Activity Program

100 Wolf Park, Winter Park, United States Show map

Offering access to entertainment venues such as Winter Park Jazz Festival, situated only 1.7 km away, the 3-bedroom Downtown Wp Chalet 100 I Private Hot Tub I Great Views I Activity Program Winter… More

From US$ 571 Book Now

3 Mi To Winter Park Slopes! Unit W/ Pool & Hot Tub

301 Lions Gate Dr Unit 114, Winter Park, United States Show map

The 2-bedroom 3 Mi To Winter Park Slopes! Unit W/ Pool & Hot Tub Villa, located approximately 5 minutes' walk from Vasquez Peak Wilderness, entices guests with an outdoor swimming pool as well as a… More

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Downtown Wp Loft 57 I Rooftop Hot Tub & Lounge I Great Views I Activity Program

57 Ski Idlewild Rd, Winter Park, United States Show map

Featuring a terrace and a patio for added enjoyment, the 3-bedroom Downtown Wp Loft 57 I Rooftop Hot Tub & Lounge I Great Views I Activity Program Winter Park villa is located just 6 minutes' walk… More

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Newly Built Ski Condo W/ Hot Tub & Shuttle Access!

Winter Park, United States Show map

The Foundry Cinema and Bowl is 400 metres from the welcoming Newly Built Ski Condo W/ Hot Tub & Shuttle Access! Winter Park villa, offering a Jacuzzi for guests' relaxation. The 2-bedroom holiday… More

From US$ 543 Book Now

Downtown Wp Loft 5 I Huge Hot Tub I Great Views I Activity Program

78311 Highway 40 #5, Winter Park, United States Show map

The 2-bedroom Luxury Loft: Mountain Views & Hot Tub Retreat Villa Winter Park, located about 5 minutes' walk from The Foundry Cinema and Bowl, can host up to 8 guests. Offering a Jacuzzi, this… More

From US$ 190 Book Now

Elk Trail Retreat

786 Elk Trail, Winter Park, United States Show map

The 2-bedroom Elk Trail Retreat Villa Winter Park is located 2.6 km from Cozens Ranch House Museum and provides a Jacuzzi. This 2-bathroom villa hosts up to 6 guests and provides them with parking. More

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Downtown Wp Penthouse 215 I Private Hot Tub I Great Views I 2 Story I Discounted Attractions

78746 Us Highway 40 #215, Winter Park, United States Show map

Up to 8 guests can stay at the 3-bedroom Downtown Wp Penthouse 215 I Private Hot Tub I Great Views I 2 Story I Discounted Attractions Villa Winter Park and enjoy Cooper Creek Square, located just a 6… More

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Mountain Home W/ Hot Tub, Near Wp Resort!

315 N Woods Pl, Winter Park, United States Show map

The 4-bedroom Mountain Home W/ Hot Tub, Near Wp Resort! Winter Park is located approximately 25 minutes' walk from Gemini Express, giving access to various tourist spots nearby. This property can… More

From US$ 1194 Book Now

Sawmill Haus Walk To Downtown Hot Tub Renovated Sleeps 9

211 Sawyer Cir, Winter Park, United States Show map

Staying at the 1-bedroom Sawmill Haus Walk To Downtown Hot Tub Renovated Sleeps 9 Villa Winter Park, guests can visit Pioneer Express, which is nearly a 10-minute ride away. The Winter Park holiday… More

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Mountain Luxury: 4Br Townhome W/ Epic Views

405 Bear Trail, Winter Park, United States Show map

The 4-bedroom Mountain Luxury: 4Br Townhome W/ Epic Views Winter Park villa is located within 3 km of Fraser Tubing Hill and provides a Jacuzzi. This Winter Park holiday home is suitable for up to 8… More

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Ski-In/Ski-Out Gemini Lift Access! Home W/ Hot Tub

145 Balsam Dr, Winter Park, United States Show map

Ski-In/Ski-Out Gemini Lift Access! Home W/ Hot Tub Winter Park enjoys a convenient location, a 12-minute walk from Winter Park Resort, and offers guests to unwind in a Jacuzzi. Guests can enjoy snow… More

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Mountain Views, Private Hot Tub And Near Winter Park

470 Kings Crossing Rd, Winter Park, Co 80482, Winter Park, United States Show map

Offering a location 3.5 km from Eskimo Express, Mountain Views, Private Hot Tub And Near Winter Park Villa gives access to various tourist spots in the area. More

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Downtown Wp Chalet 366 I Private Hot Tub I Great Views I Activity Program

366 Lake Trail, Winter Park, United States Show map

Downtown Wp Chalet 366 I Private Hot Tub I Great Views I Activity Program Winter Park enjoys a convenient location, about a 20-minute walk from Cooper Creek Square, and offers guests to unwind in a… More

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New Luxury Loft 6 I Huge Hot Tub I Great Views I Best Price I Free Adventures Daily

Winter Park, United States Show map

Offering a location merely 5 minutes' walk from The Foundry Cinema and Bowl, Luxury Loft: Mountain Views & Hot Tub Retreat Villa Winter Park gives access to various tourist spots in the area. More

From US$ 198 Book Now

Whisk Away To Winter Park 2 Bdr 5 Min From Skiing

197 Village Dr, Winter Park, United States Show map

The 2-bedroom Whisk Away To Winter Park 2 Bdr 5 Min From Skiing villa provides a patio and a golf course for guests' leisure, and is around a 20-minute walk from Cooper Creek Square. Suitable for up… More

From US$ 267 Book Now

New Luxury Condo 1305 Hot Tub Ac Great Views Best Price 500 Dollars Free Activities Daily

144 Ski Idlewild Dr #1305, Winter Park, United States Show map

The 3-bedroom New Luxury Condo 1305 Hot Tub Ac Great Views Best Price 500 Dollars Free Activities Daily Winter Park villa is located merely 1.8 km from Cozens Ranch House Museum and provides a… More

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Woodsy Winter Park Condo W/ Pool & Hot Tub Access

301 Lions Gate Dr Unit 107, Winter Park, United States Show map

The 3-bedroom Woodsy Winter Park Condo W/ Pool & Hot Tub Access villa, located within 5 minutes' walk of Vasquez Peak Wilderness, entices guests with an outdoor swimming pool as well as a Jacuzzi to… More

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Winterfell At Winter Park Resort

321 N Woods Pl, Winter Park, United States Show map

Offering access to entertainment venues such as The Foundry Cinema and Bowl, situated approximately a 10-minute drive away, the 1-bedroom Winterfell At Winter Park Resort villa can host up to 12… More

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Winter Park Condo W/ Shuttle To Slopes!

78415 Us-40 Unit 4, Winter Park, United States Show map

The 2-bedroom Winter Park Condo W/ Shuttle To Slopes! villa is located about 10 minutes' drive from Fraser Tubing Hill and provides an indoor pool. With a maximum capacity of 5 guests, the… More

From US$ 220 Book Now

Downtown Winter Park Condo ~ 3 Mi To Skiing!

144 Ski Idlewild Rd Unit 1406, Winter Park, United States Show map

The 2-bedroom Downtown Winter Park Condo ~ 3 Mi To Skiing! villa offers proximity to such city sites as Cooper Creek Square, located nearly a 5-minute walk away. Providing guests with Wi-Fi and a… More

From US$ 512 Book Now

Winter Park Pond Chalet 13 I Private Hot Tub I Gas Firepit I Fantastic Views I Arcade Games I Activity Program

13 Beavers Lodge Rd, Winter Park, United States Show map

Located 10 minutes' drive from the outdoor sports store "Colorado Adventure Park", Winter Park Pond Chalet 13 I Private Hot Tub I Gas Firepit I Fantastic Views I Arcade Games I Activity Program… More

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Crestview Place Mountain View Balcony & Shuttle

79050 Us Highway 40 Unit 303, Winter Park, United States Show map

The 2-bedroom Crestview Place Mountain View Balcony & Shuttle Winter Park villa, located around a 5-minute walk from Hideaway Park, can host up to 6 guests. This accommodation features opportunities… More

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Hike, Bike, Ski: Winter Park Condo W/ Deck

126 Hi Country Dr Unit 18-10, Winter Park, United States Show map

Located merely 1.5 km from Ski Idlewild Abondoned Chairlift, the 2-bedroom Hike, Bike, Ski: Winter Park Condo W/ Deck villa provides access to various tourist attractions in the vicinity. Offering… More

From US$ 220 Book Now

Downtown Wp Condo 3202 I Private Hot Tub I Ac I Great Views I Activity Program

144 Ski Idlewild Rd. #3202, Winter Park, United States Show map

The 3-bedroom Downtown Wp Condo 3202 I Private Hot Tub I Ac I Great Views I Activity Program Winter Park villa is situated approximately 5 minutes' walk from Cooper Creek Square, featuring such… More

From US$ 1600 Book Now

Downtown Wp Loft 106 I Huge Hot Tub I Great Views I Activity Program

400 Baker Dr. #106, Winter Park, United States Show map

Up to 9 guests can stay at the 3-bedroom Downtown Wp Loft 106 I Huge Hot Tub I Great Views I Activity Program Villa Winter Park and enjoy The Foundry Cinema and Bowl, located merely 6 minutes' walk… More

From US$ 389 Book Now

45 Idlewild

45 Idlewild Lane, Winter Park, United States Show map

The 2-bedroom 45 Idlewild Villa Winter Park offers quick access to such city attractions as Hideaway Park, located just a 7-minute walk away. Offering balloon rides, this Winter Park holiday home can… More

From US$ 445 Book Now

Fraser Crossing 3405 | Steps To Gondola

670 Winter Park Dr Unit 3405, Winter Park, United States Show map

Fraser Crossing 3405 | Steps To Gondola Winter Park villa offers swift access to various city sites, such as Amaze'n Mazes Colorado Amusement Center, situated approximately 5 minutes' walk away. More

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Red Quill Village

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

The 4-bedroom Red Quill Village Winter Park villa is located approximately a 10-minute drive from the outdoor sports store "Colorado Adventure Park" and provides a hot tub. The Winter Park holiday… More

From US$ 654 Book Now

Downtown Wp Sojourn Villa 115 | Bunk Room | Great Views | Discounted Attractions

115 Wheeler Rd., Winter Park, United States Show map

The 3-bedroom Downtown Wp Sojourn Villa 115 | Bunk Room | Great Views | Discounted Attractions Winter Park offers easy access to such tourist spots as Ski Idlewild Abondoned Chairlift, located a mere… More

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'The Mountain Chalet' - Free Ski Shuttle To Lifts!

900 Vasquez Rd Unit 3, Winter Park, United States Show map

Offering a location 4.8 km from Eagle Wind, 'The Mountain Chalet' - Free Ski Shuttle To Lifts! Winter Park gives access to various tourist spots in the area. More

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Downtown Wp Pond Chalet 9 I Private Hot Tub I Great Views I Gas Firepit I Discounted Attractions

9 Beaver Lodge Rd, Winter Park, United States Show map

Offering a Jacuzzi for a relaxing experience, the 4-bedroom Downtown Wp Pond Chalet 9 I Private Hot Tub I Great Views I Gas Firepit I Discounted Attractions Winter Park is located about a 25-minute… More

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Winter Park Resort Home 2225 I Private Hot Tub I Great Views I Bunk Room I Activity Program

2225 Lakota Trail, Winter Park, United States Show map

Located a mere 8 minutes' stroll from Main Street, the 6-bedroom Winter Park Resort Home 2225 I Private Hot Tub I Great Views I Bunk Room I Activity Program can accommodate up to 16 guests, providing… More

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The Grand Timberlake Lodge - Hot Tub - Sauna

355 Moose Trail, Winter Park, United States Show map

Accommodating up to 4 guests, the 2-bedroom The Grand Timberlake Lodge - Hot Tub - Sauna Winter Park is situated around a 10-minute ride from renowned cultural sites such as Fraser Valley Public… More

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Downtown Wp Condo 412 I Pool I Game Room I Hot Tub I Views I Bunk Room I Discounted Attractions

401 Trailhead Circle #412, Winter Park, United States Show map

Offering access to entertainment venues such as Winter Park Jazz Festival, situated approximately a 15-minute walk away, the 2-bedroom Luxury Condo 412: Pool, Club & Views with Activity Perks Winter… More

From US$ 181 Book Now

Divide View Townhome

Winter Park, United States Show map

Situated approximately a 20-minute walk from Cooper Creek Square, the 3-bedroom Divide View Townhome Winter Park villa entices guests to explore various tourist attractions in the area. Suitable for… More

From US$ 276 Book Now