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2026-11-03
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Holiday Homes in Winter Park

Ski-In/Ski-Out! Winter Park Family Gem W/ Hot Tub

422 Iron Horse Way Unit 204, Winter Park, United States Show map

Offering a Jacuzzi, the 2-bedroom Ski-In/Ski-Out! Winter Park Family Gem W/ Hot Tub villa is located nearly a 25-minute walk from Looking Glass. Offering balloon tours, this property can accommodate… More

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Steps To Free Ski Shuttle! Dtwn Winter Park Condo

301 Lions Gate Dr Unit 104, Winter Park, United States Show map

The 3-bedroom Steps To Free Ski Shuttle! Dtwn Winter Park Condo villa offers quick access to such tourist spots as Vasquez Peak Wilderness, situated merely a 5-minute walk away. Featuring a Jacuzzi… More

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Downtown Wp Venue Loft 92 I Rooftop Hot Tub I Great Views I Activity Program

92 Rendezvous Way, Winter Park, United States Show map

The 4-bedroom New Hideaway Park Luxury Loft: Rooftop Hot Tub & Activity Perks Winter Park villa is situated around 5 minutes' walk from Vasquez Peak Wilderness and offers guests to relax with a hot… More

From US$ 568 Book Now

Walk To Hideaway Park! All-Season Winter Park Gem

301 Lions Gate Dr Unit 115, Winter Park, United States Show map

Staying at the 3-bedroom Walk To Hideaway Park! All-Season Winter Park Gem villa, guests can visit Vasquez Peak Wilderness, which is only 200 metres away. The Winter Park holiday home offers an… More

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Downtown Wp Villa 165 I Private Hot Tub I Great Views I Bunk Room I Activity Program

165 Whistlestop Circle, Winter Park, United States Show map

The 4-bedroom Downtown Wp Villa 165 I Private Hot Tub I Great Views I Bunk Room I Activity Program Winter Park is situated only 1.1 km from Cozens Ranch House Museum and provides a Jacuzzi, ensuring… More

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Downtown Wp Villa 206 I Private Hot Tub I Views I Activity Program

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

During the stay at Downtown Wp Villa 206 I Private Hot Tub I Views I Activity Program Winter Park, guests can indulge in snow skiing and mini golf or visit the outdoor sports store "Colorado… More

From US$ 535 Book Now

Downtown Wp Loft 4 I Huge Hot Tub I Great Views I Activity Program

78311 Us 40 Unit 4, Winter Park, United States Show map

Suitable for 8 guests, the 2-bedroom Downtown Wp Loft 4 I Huge Hot Tub I Great Views I Activity Program Villa Winter Park is located nearly a 5-minute walk from Cozens Ranch House Museum and provides… More

From US$ 450 Book Now

Founders Pointe 4471 Ski In Ski Out Winter Park Resort

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

Located within 20 minutes' walk of Moffat Tunnel, Founders Pointe 4471 Ski In Ski Out Winter Park Resort villa entices guests to relax in a Jacuzzi. Along with a lift and a vending machine, this… More

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Winter Park Resort Villa 200 I Private Hot Tub I Great Views I Bunk Room I Activity Program

200 Antler Way, Winter Park, United States Show map

Winter Park Resort Villa 200 I Private Hot Tub I Great Views I Bunk Room I Activity Program is located a 16-minute walk from Winter Park Resort and provides a Jacuzzi. Offering balloon tours, the 5… More

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Winter Park Condo With Fireplace, Centrally Located

159 Hi Country Dr Bldg 19 Unit 13, Winter Park, Co 80482, Usa, Winter Park, United States Show map

The 2-bedroom Winter Park Condo With Fireplace, Centrally Located villa is located only 1 km from Cozens Ranch House Museum and provides an indoor pool. This Winter Park holiday home hosts up to 4… More

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Luxury Chalet 106 I Hot Tub I Great Views I Best Price I Free Adventures Daily

106 Lookout Point, Winter Park, United States Show map

Situated 10 minutes' drive from Olympia Express, Luxury Chalet 106 I Hot Tub I Great Views I Best Price I Free Adventures Daily Winter Park provides access to numerous tourist attractions in the area. More

From US$ 477 Book Now

Condo 3 Mi To Winter Park Resort: Community Perks!

301 Lions Gate Dr Unit 120, Winter Park, United States Show map

The 3-bedroom Condo 3 Mi To Winter Park Resort: Community Perks! villa, located only 5 minutes' walk from Vasquez Peak Wilderness, can host up to 8 guests. Featuring a Jacuzzi, this property is in… More

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Mtn Base W/ Hot Tub Access Near Winter Park Resort

301 Lions Gate Dr Unit 124, Winter Park, United States Show map

The 3-bedroom Mtn Base W/ Hot Tub Access Near Winter Park Resort villa, located around a 5-minute walk from Vasquez Peak Wilderness, can host up to 8 guests. Offering a Jacuzzi and a sauna, this… More

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Riverfront Retreat With Hot Tubs And Walk To Downtown Winter Park

51 River Dr, Winter Park, Co 80482, Winter Park, United States Show map

The 3-bedroom Riverfront Retreat With Hot Tubs And Walk To Downtown Winter Park villa offers quick access to such city attractions as The Foundry Cinema and Bowl, located merely 6 minutes' walk away. More

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Colorado Ski Condo In The Heart Of Winter Park

189 Village Dr 933, Winter Park, United States Show map

Situated about 10 minutes' drive from Cozens Ranch House Museum, 2-bedroom Colorado Ski Condo In The Heart Of Winter Park villa offers guests to enjoy a patio and grill. Featuring a hot tub and a… More

From US$ 295 Book Now

Home Spa Retreat Downtown Wp Walk To Shops Dining

103 Ramble Lane, Winter Park, United States Show map

During the stay at Home Spa Retreat Downtown Wp Walk To Shops Dining Winter Park, guests can indulge in a Jacuzzi or visit Cozens Ranch House Museum, located a 10-minute drive away. More

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Winter Park Penthouse 141 I Private Rooftop Amenity Plaza I Amazing Views I Discounted Attractions

141 Ski Idlewild Rd., Winter Park, United States Show map

During the stay at Winter Park Penthouse 141 I Private Rooftop Amenity Plaza I Amazing Views I Discounted Attractions villa, guests can indulge in a Jacuzzi or visit Main Street, located 3.6 km away.… More

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New Luxury Condo 2202 I Hot Tub I Ac I Great Views I Best Price I Free Adventures Daily

144 Ski Idlewild Rd. #2202, Winter Park, United States Show map

Situated 1.8 km from Cozens Ranch House Museum, Luxury Condo 2202: Hot Tub, AC & Views with Activity Perks Winter Park villa provides access to numerous tourist attractions in the area. More

From US$ 403 Book Now

Luxury Villa 568 I Hot Tub I Great Views I Best Price I Free Adventures Daily

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

Luxury Villa 568 I Hot Tub I Great Views I Best Price I Free Adventures Daily Winter Park enjoys a convenient location, an 18-minute walk from Hideaway Park, and offers guests to unwind in a Jacuzzi.… More

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Trailside Tranquility

1420 Bear Trail, Winter Park, United States Show map

Featuring balloon rides to make your visit more entertaining, Trailside Tranquility Villa Winter Park is 4.8 km from High Lonesome Express. Guests can enjoy snow skiing and fisheries at this 3… More

From US$ 498 Book Now

Luxury 4 Bedroom Cabin: 2 King Suites On Shuttle Route

Winter Park, Co, 80452, Winter Park, United States Show map

Situated about 10 minutes by car from Cozens Ranch House Museum, Luxury 4 Bedroom Cabin: 2 King Suites On Shuttle Route Winter Park offers guests to enjoy playground and a dining table. Featuring a… More

From US$ 704 Book Now

Ridgeview Retreat Steps To Hideaway Park And Town

404 Sawyer Cir, Winter Park, Co 80482, Winter Park, United States Show map

Situated about 10 minutes by car from the outdoor sports store "Colorado Adventure Park", Ridgeview Retreat Steps To Hideaway Park And Town Villa Winter Park provides access to numerous tourist… More

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3 Mi To Winter Park Resort! Mtn-View Condo

301 Lions Gate Dr Unit 118, Winter Park, United States Show map

The 3-bedroom 3 Mi To Winter Park Resort! Mtn-View Condo villa, located about a 5-minute walk from Vasquez Peak Wilderness, invites guests to relax in a Jacuzzi. More

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Downtown Wp Corner Loft 24 I Hot Tub I Great Views I Bunk Beds I Activity Program

78321 Us Hwy 40 #24, Winter Park, United States Show map

Along with proximity to Cozens Ranch House Museum, located only 9 minutes' stroll away, the 2-bedroom Luxury Loft: Hot Tub Retreat with Views & Activities Villa Winter Park provides access to a… More

From US$ 191 Book Now

Elk Run Half Duplex With Views

952 Elk Trail Unit A, Winter Park, United States Show map

Located only 1.5 km from Vasquez Peak Wilderness, Elk Run Half Duplex With Views Villa Winter Park provides access to various tourist attractions in the vicinity. More

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Red Quill 105

105 Red Quill Way, Unit 105, Winter Park, United States Show map

Located about a 10-minute drive from the outdoor sports store "Colorado Adventure Park", Red Quill 105 Villa Winter Park provides access to various tourist attractions in the vicinity. More

From US$ 359 Book Now

Downtown Wp Townhome 101 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions

101 Sawyer Circle, Winter Park, United States Show map

Downtown Wp Townhome 101 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions Winter Park villa offers proximity to nearby tourist spots, such as Endeavour Lift, situated around 10… More

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Downtown Wp Villa 709 I Private Hot Tub I Views I Bunk Room I Desk I Activity Program

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

The 3-bedroom Downtown Wp Villa 709 I Private Hot Tub I Views I Bunk Room I Desk I Activity Program Winter Park is located nearly a 10-minute drive from Fraser Tubing Hill and provides a Jacuzzi. More

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Condo W/ Pool + Hot Tub - Walk To Dt Winter Park!

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

Condo W/ Pool + Hot Tub - Walk To Dt Winter Park! villa is located around 10 minutes by car from Main Street and provides hiking for active guests. Offering a hot tub, this welcoming property is 4.8… More

From US$ 215 Book Now

Downtown Wp Riverfront Chalet 280 I Rooftop Hot Tub I Great Views I Theatre I Discounted Attractions

280 Sawyer Circle, Winter Park, United States Show map

Located 20 minutes' walk from Hideaway Park, Downtown Wp Riverfront Chalet 280 I Rooftop Hot Tub I Great Views I Theatre I Discounted Attractions Winter Park entices guests to relax in a hot tub. More

From US$ 1156 Book Now

Trail Blaze & Unwind! Winter Park Condo W/ Pool

301 Lions Gate Dr Unit 121, Winter Park, United States Show map

The 3-bedroom Trail Blaze & Unwind! Winter Park Condo W/ Pool villa, located approximately a 5-minute walk from Vasquez Peak Wilderness, can host up to 8 guests. Offering a Jacuzzi, this… More

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Downtown Wp Condo 814 I Pool I Game Room I Hot Tub I Views I Bunk Room I Activity Program

801 Trailhead Circle #814, Winter Park, United States Show map

The 2-bedroom Downtown Wp Condo 814 I Pool I Game Room I Hot Tub I Views I Bunk Room I Activity Program Winter Park villa, located only a 6-minute walk from Vasquez Peak Wilderness, can host up to 6… More

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Winter Park Resort Villa 217 I Private Hot Tub I Great Views I Bunk Room I Activity Program

217 Lakota Park Dr., Winter Park, United States Show map

Offering a Jacuzzi for a relaxing experience, the 4-bedroom Winter Park Resort Villa 217 I Private Hot Tub I Great Views I Bunk Room I Activity Program is located approximately a 25-minute walk from… More

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New Luxury River Front Villa 92 I Rooftop Lounge I Hot Tub I Views I Free Adventures Daily

92 Ramble Lane, Winter Park, United States Show map

Offering a terrace and barbecue for guests' leisure, New Luxury River Front Villa 92 I Rooftop Lounge I Hot Tub I Views I Free Adventures Daily Winter Park is situated 6 km from Fraser Valley Public… More

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Winterhaven Estate By Avantstay

325 Lake Trail, Winter Park, United States Show map

During the stay at the 11-bedroom Winterhaven Estate By Avantstay Winter Park villa, guests can indulge in a Jacuzzi or visit Winter Park Resort, located nearly 10 minutes' drive away. More

From US$ 3657 Book Now

Walkable Winter Park Gem, Downtown With Amenities

301 Trailhead Circle #322 Winter Park, Co 80482, Winter Park, United States Show map

Situated approximately 5 minutes on foot from Winter Park Jazz Festival, the 2-bedroom Walkable Winter Park Gem, Downtown With Amenities Villa offers quick access to numerous city landmarks nearby. More

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Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I Free Adventures Daily

71 Balsam Dr., Winter Park, United States Show map

Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I Free Adventures Daily Winter Park is located about a 20-minute walk from Coca Cola Tubing Hill At Winter Park and provides… More

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Slopeside Villa 125 I Private Hot Tub I Ski Views I Activity Program

125 Balsam Drive, Winter Park, United States Show map

Featuring a Jacuzzi, the 3-bedroom Slopeside Villa 125 I Private Hot Tub I Ski Views I Activity Program Winter Park is located approximately 10 minutes' walk from Main Street and can host up to 8… More

From US$ 626 Book Now

Slopeside Luxury Villa 82 I Hot Tub I Great Views I Best Price I Free Adventures Daily

82 Trademark Dr., Winter Park, United States Show map

Situated a mere 6 minutes' walk from Main Street, the 3-bedroom Slopeside Luxury Villa 82 I Hot Tub I Great Views I Best Price I Free Adventures Daily Winter Park offers a Jacuzzi and can accommodate… More

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Hot Tub & Amazing Views: Luxury Winter Park Haven!

26 Sunny Ridge Ln, Winter Park, United States Show map

The 3-bedroom Hot Tub & Amazing Views: Luxury Winter Park Haven! Villa is situated approximately 500 metres from Ski Idlewild Abondoned Chairlift and offers guests to relax with a Jacuzzi. Offering… More

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Downtown Wp Villa 491 I Great Views I Pet Friendly I Activity Program

491 Timber Lake Way, Winter Park, United States Show map

With the capacity to host 7 guests, the 3-bedroom Downtown Wp Villa 491 I Great Views I Pet Friendly I Activity Program Winter Park is located about 25 minutes on foot from such significant cultural… More

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3Br Riverfront Retreat! Mtn Views, Community Perks

507 Hi Country Dr Unit 7-87, Winter Park, United States Show map

3Br Riverfront Retreat! Mtn Views, Community Perks Winter Park villa provides an opportunity to stay a 6-minute walk from Saint Bernard of Montjoux Catholic Church and offers a Jacuzzi and an indoor… More

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Winter Park Resort Villa 403 I Private Hot Tub I Great Views I Game Room I Discounted Attractions

403 Reserve Way, Winter Park, United States Show map

Offering a steam room, a hot tub, and a sauna, the 5-bedroom Luxury Villa #403: Resort-Adjacent with Hot Tub and Activity Perks Winter Park is situated a mere 9 minutes' walk from Winter Park Resort… More

From US$ 707 Book Now

Downtown Wp Villa 85 I Hot Tub I Rooftop Lounge I Great Views I Bunk Room I Discounted Attractions

85 Ramble Lane, Winter Park, United States Show map

During the stay at Downtown Wp Villa 85 I Hot Tub I Rooftop Lounge I Great Views I Bunk Room I Discounted Attractions Winter Park, guests can indulge in a Jacuzzi or visit the outdoor sports store… More

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Downtown Wp Loft 21 I Rooftop Lounge & Hot Tub I Great Views I Activity Program

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

The 3-bedroom Luxury Loft 21: Rooftop Retreat with Complimentary Activities Winter Park villa is located 2.5 km from Cozens Ranch House Museum and provides snow skiing and mini golf for active guests… More

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Ski In Out Condo 4549 I Huge Hot Tub I Views I Heated Garage I Activity Program

580 Winter Park Dr. 4549, Winter Park, United States Show map

Welcoming guests with a Jacuzzi, the 2-bedroom Ski In Out Condo 4549 I Huge Hot Tub I Views I Heated Garage I Activity Program Winter Park villa is located around 5 minutes' walk from Winter Park… More

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Lakota Northwoods Luxury Villa 308

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

With the capacity to host 12 guests, the 4-bedroom Lakota Northwoods Luxury Villa 308 Winter Park is located about a 15-minute ride from such significant cultural landmarks as Cozens Ranch House… More

From US$ 1535 Book Now

Downtown Wp Townhome 108 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions

108 Sawyer Circle, Winter Park, United States Show map

Situated just 5 minutes' stroll from Winter Park Jazz Festival, Downtown Wp Townhome 108 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions Winter Park villa offers quick access to… More

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Hot Tub! Walkable Condo 3 Mi To Winter Park Resort

301 Lions Gate Dr Unit 123, Winter Park, United States Show map

The 3-bedroom Hot Tub! Walkable Condo 3 Mi To Winter Park Resort villa offers quick access to such tourist spots as Vasquez Peak Wilderness, situated only a 5-minute walk away. Offering a Jacuzzi… More

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Downtown Wp Villa 282 I Rooftop Hot Tub I Great Views I Activity Program

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

The 4-bedroom Downtown Wp Villa 282 I Rooftop Hot Tub I Great Views I Activity Program Winter Park is located around 10 minutes by car from the outdoor sports store "Colorado Adventure Park" and… More

From US$ 899 Book Now