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2026-11-03
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Holiday Homes in Winter Park

Modern Mountain Escape

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

Offering a Jacuzzi, the 5-bedroom Modern Mountain Escape Villa Winter Park is located about 25 minutes' walk from Super Gauge. Offering horse riding tours, the holiday home can accommodate up to 16… More

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Founders Pointe Winter Park Base Massive Hot Tub

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

The cosy Founders Pointe 4569 | Ski-In/Ski-Out Winter Park villa provides easy access to various city attractions, such as Alpine Slide, situated around 5 minutes' walk away. More

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Downtown Wp Villa 145 I Hot Tub I Views I Bunks I Fire Table I Mini Bar I Discounted Attractions

145 Whistlestop Circle, Winter Park, United States Show map

The 3-bedroom Downtown Wp Villa 145 I Hot Tub I Views I Bunks I Fire Table I Mini Bar I Discounted Attractions Winter Park is situated just 6 minutes' walk from Vasquez Peak Wilderness, featuring… More

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Downtown Wp Villa 1 I Private Hot Tub I Views I Activity Program

311 Vasquez Dr. #1, Winter Park, United States Show map

Situated within a 10-minute drive of Fraser Tubing Hill, the 3-bedroom Luxury Townhome Retreat: Mountain Views & Hot Tub Escape Winter Park villa offers guests to enjoy playground and a golf course. More

From US$ 516 Book Now

Walk To Ski Shuttle! Ideal Winter Park Base Camp

301 Lions Gate Dr Unit 101, Winter Park, United States Show map

Located approximately 5 minutes' walk from Vasquez Peak Wilderness, the 3-bedroom Walk To Ski Shuttle! Ideal Winter Park Base Camp villa features a swimming pool, a Jacuzzi, ensuring a relaxing stay. More

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Spacious Village View Townhouse With Fireplace At Parry Peak Lofts Townhouse

115 Parry Peak Way, Winter Park, United States Show map

Along with proximity to Winter Park Resort, merely 450 metres away, the 3-bedroom Spacious Village View Townhouse With Fireplace At Parry Peak Lofts Townhouse Winter Park villa offers opportunities… More

From US$ 1708 Book Now

New Luxury Chalet 139 I Hot Tub I Great Views I Best Price I Free Adventures Daily

139 Stagecoach Way, Winter Park, United States Show map

Luxury Chalet #139: Hot Tub Retreat with Scenic Views Winter Park is located just 1.5 km from Cozens Ranch House Museum, giving access to various tourist spots nearby. More

From US$ 358 Book Now

Downtown Wp Corner Loft 25 I Huge Hot Tub I Great Views I Bunk Beds I Discounted Attractions

78321 Highway 40 #25, Winter Park, United States Show map

Situated only 6 minutes' walk from The Foundry Cinema and Bowl, the 2-bedroom Downtown Wp Corner Loft 25 I Huge Hot Tub I Great Views I Bunk Beds I Discounted Attractions Villa Winter Park offers… More

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

50 Village Drive, Winter Park, Co 80482, Us, Winter Park, United States Show map

During the stay at the welcoming Condo W/ Pool Access: 2 Mi To Winter Park Resort! villa, guests can indulge in a Jacuzzi or visit Winter Park Resort, located a 10-minute ride away. Located 4 km from… More

From US$ 402 Book Now

Luxury Chalet #1240 With Hot Tub & Great Views - 500 Dollars Of Free Activities & Equipment Rentals Daily

Winter Park, United States Show map

Nestled 3 km from Fraser Tubing Hill, Luxury Chalet #1240 With Hot Tub & Great Views - 500 Dollars Of Free Activities & Equipment Rentals Daily Winter Park entices guests to explore various tourist… More

From US$ 481 Book Now

Dreamcatcher At Lakota Home

Winter Park, United States Show map

Offering guests to unwind in a Jacuzzi, Dreamcatcher At Lakota Home Winter Park is located an 18-minute walk from Winter Park Resort. Guests can enjoy snow skiing, hiking, and cycling at this villa… More

From US$ 1794 Book Now

Walk To Cooper Creek Square: Condo W/ Hot Tub!

78746 U.S. Hwy 40 Unit 217, Winter Park, United States Show map

The 2-bedroom Walk To Cooper Creek Square: Condo W/ Hot Tub! Winter Park villa is situated merely a 6-minute stroll from Cooper Creek Square, featuring such comforts as Wi-Fi and parking. Offering a… More

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Downtown Wp Condo 2403 I Hot Tub I Views I Ac I Gas Firepit I Bunk Room I Discounted Attractions

144 Ski Idlewild Rd. #2403, Winter Park, United States Show map

The 2-bedroom Downtown Wp Condo 2403 I Hot Tub I Views I Ac I Gas Firepit I Bunk Room I Discounted Attractions Winter Park villa offers easy access to such tourist spots as Cooper Creek Square… More

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Ski In Out Villa 452 I Private Hot Tub I Great Views I Activity Program

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

During the stay at the 4-bedroom Ski-In/Ski-Out Luxury Villa with Hot Tub and Mountain Views Winter Park, guests can indulge in snow skiing and mini golf or visit Winter Park Resort, located… More

From US$ 1693 Book Now

Hot Tub & Heated Pool! Ski Retreat In Winter Park

301 Lions Gate Dr Unit 103, Winter Park, United States Show map

During the stay at Hot Tub & Heated Pool! Ski Retreat In Winter Park villa, guests can indulge in a Jacuzzi or visit Fraser Tubing Hill, located 2.9 km away. Providing guests with Wi-Fi and parking… More

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Charming Winter Park Condo - Steps To Slopes!

580 Winter Park Dr Unit 4349, Winter Park, United States Show map

The 2-bedroom Charming Winter Park Condo - Steps To Slopes! villa entices guests to enjoy snow skiing and offers proximity to Winter Park Resort, located nearly a 5-minute stroll away. Featuring a… More

From US$ 1120 Book Now

Downtown Wp River Front Villa 232 I Private Hot Tub I Great Views I Activity Program

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

The 4-bedroom Riverside Luxury Villa: Hot Tub, Views & Activity Perks Winter Park is nestled approximately 5 minutes on foot from Cooper Creek Square and entices guests with a hot tub. Located 4.8 km… More

From US$ 752 Book Now

Steps From Ski Shuttle! Wp Condo W/ Heated Pool

301 Lions Gate Dr Unit 125, Winter Park, United States Show map

Located 16 minutes' walk from Cozens Ranch House Museum, Steps From Ski Shuttle! Wp Condo W/ Heated Pool Winter Park villa has an outdoor swimming pool and is ideal for up to 8 guests. The 3-bedroom… More

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Slopeside Sanctuary - Penthouse < 1 Mi To Lifts!

97 Kinney Way Unit C, Winter Park, United States Show map

Featuring a hot tub, the 3-bedroom Slopeside Sanctuary - Penthouse 1 Mi To Lifts! Villa Winter Park is located around 10 minutes' walk from Main Street and can host up to 12 guests. Providing guests… More

From US$ 1295 Book Now

Winter Park Ski Haus

148 Fir Drive, Winter Park, United States Show map

Featuring balloon tours to make your visit more entertaining, the 6-bedroom Winter Park Ski Haus is in the immediate vicinity of Endeavour Lift. Guests can enjoy snow skiing, hiking, and billiard at… More

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Downtown Wp Condo 3203 I Hot Tub I Ac I Great Views I Activity Program

144 Ski Idlewild Rd #3203, Winter Park, United States Show map

Downtown Wp Condo 3203 I Hot Tub I Ac I Great Views I Activity Program Winter Park villa is 5 minutes' walk from Hideaway Park, offering guests to unwind at a Jacuzzi. Located fairly close to Cooper… More

From US$ 589 Book Now

Winter Park Resort Villa 211 I Private Hot Tub I Great Views I Arcade I Discounted Attractions

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

During the stay at the 4-bedroom Winter Park Resort Villa 211 I Private Hot Tub I Great Views I Arcade I Discounted Attractions, guests can indulge in a Jacuzzi or visit Cozens Ranch House Museum… More

From US$ 1092 Book Now

53 East Viking Drive

53 East Viking Drive, Winter Park, United States Show map

During the stay at the 3-bedroom 53 East Viking Drive Villa Winter Park, guests can indulge in snow skiing, hiking, and fisheries or visit the outdoor sports store "Colorado Adventure Park", located… More

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Downtown Wp Loft 16 I Huge Hot Tub I Great Views I Activity Program

78321 Us Hwy 40 #16, Winter Park, United States Show map

Luxury Loft #16: Hot Tub Retreat with Complimentary Activities Villa Winter Park is situated 9 minutes' walk from Cozens Ranch House Museum and provides a hot tub for a relaxing stay. Suitable for 8… More

From US$ 283 Book Now

Downtown Wp Townhome 124 I Private Hot Tub I Great Views I Activity Program

124 Loggers Lane, Winter Park, United States Show map

During the stay at the 2-bedroom Downtown Wp Townhome 124 I Private Hot Tub I Great Views I Activity Program Winter Park villa, guests can indulge in snow skiing and mini golf or visit Fraser Tubing… More

From US$ 629 Book Now

Downtown Wp Villa 296 I Rooftop Hot Tub I Great Views I Activity Program

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

Situated just 5 minutes on foot from Vasquez Peak Wilderness, the 4-bedroom Downtown Wp Villa 296 I Rooftop Hot Tub I Great Views I Activity Program Winter Park offers quick access to numerous city… More

From US$ 319 Book Now

Ski In Out Penthouse 4675 I Huge Hot Tub I Great Views I Activity Program

580 Winter Park Dr. #4675, Winter Park, United States Show map

Ski In Out Penthouse 4675 I Huge Hot Tub I Great Views I Activity Program Winter Park villa is situated a 5-minute walk from Winter Park Resort and offers a Jacuzzi, ensuring a more relaxing stay. More

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Downtown Wp River Front Villa 110 I Rooftop Hot Tub & Lounge I Great Views I Activity Program

110 Ramble Lane, Winter Park, United States Show map

The 2-bedroom Riverside Luxury Villa: Hot Tub Retreat with Activity Perks Winter Park is located about a 10-minute drive from Fraser Tubing Hill and provides a Jacuzzi. This Winter Park villa… More

From US$ 525 Book Now

Downtown Wp Villa 135 I Hot Tub I Great Views I Bunk Room I Desk I Discounted Attractions

135 Stagecoach Way, Winter Park, United States Show map

During the stay at Downtown Wp Villa 135 I Hot Tub I Great Views I Bunk Room I Desk I Discounted Attractions Winter Park, guests can indulge in a Jacuzzi or visit Fraser Tubing Hill, located a 10… More

From US$ 259 Book Now

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

720 Baker Dr. #206, Winter Park, United States Show map

During the stay at Downtown Wp Condo 206 I Huge Hot Tub I Great Views I Activity Program Winter Park villa, guests can indulge in a Jacuzzi or visit the outdoor sports store "Colorado Adventure Park"… More

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Ski In Out Villa 492 I Private Hot Tub I Great Views I Activity Program

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

Offering a hot tub for a relaxing experience, the 4-bedroom Ski In Out Luxury Villa: Mountain Retreat with Hot Tub & Views Winter Park is located 16 minutes' walk from Winter Park Resort. Providing… More

From US$ 692 Book Now

Steps To Dtwn! Resort-Style Winter Park Getaway

490 Kings Crossing Rd Unit 632, Winter Park, United States Show map

During the stay at the 2-bedroom Steps To Dtwn! Resort-Style Winter Park Getaway villa, guests can indulge in a Jacuzzi, a sauna, and an indoor pool or visit the outdoor sports store "Colorado… More

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Downtown Winter Park Townhouse 3 Mi To Ski Resort!

124 Logger Lane, Winter Park, United States Show map

Situated approximately a 15-minute walk from Winter Park Jazz Festival, Downtown Winter Park Townhouse 3 Mi To Ski Resort! villa entices guests to explore various tourist attractions in the area. More

From US$ 1016 Book Now

Winter Park Resort Villa 401 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions

401 Reserve Way, Winter Park, United States Show map

Offering a hot tub, the 5-bedroom Luxury Villa Retreat: Hot Tub, Views & Complimentary Activities Winter Park is situated merely a 9-minute walk from Winter Park Resort and can accommodate 21 people. More

From US$ 1213 Book Now

Winter Park Resort Villa 509 I Hot Tub I Great View I Theatre I Fire Table I Discounted Attractions

509 Summit Pl, Winter Park, United States Show map

During the stay at Winter Park Resort Villa 509 I Hot Tub I Great View I Theatre I Fire Table I Discounted Attractions, guests can indulge in a Jacuzzi or visit Coca Cola Tubing Hill At Winter Park… More

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Shuttle To Winter Park Resort! Group Condo W/ Pool

301 Lions Gate Dr Unit 108, Winter Park, United States Show map

The 3-bedroom Shuttle To Winter Park Resort! Group Condo W/ Pool villa, located nearly a 5-minute walk from Vasquez Peak Wilderness, can host up to 8 guests. Featuring a Jacuzzi, the property is in… More

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Hot Tub Access: Condo 2 Mi To Winter Park Resort!

50 Village Dr Unit 3-11, Winter Park, United States Show map

Hot Tub Access: Condo 2 Mi To Winter Park Resort! villa offers proximity to nearby tourist spots, such as Be.. Boutique, situated about 800 metres away. Featuring a Jacuzzi, a sauna, and an indoor… More

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Downtown Wp Loft 308 I Huge Hot Tub I Great Views I Activity Program

400 Baker Dr. #308, Winter Park, United States Show map

The 2-bedroom Luxury Loft 308: Mountain Views & Hot Tub Retreat Villa Winter Park, located about a 5-minute walk from The Foundry Cinema and Bowl, can host up to 15 guests. Featuring a Jacuzzi, this… More

From US$ 400 Book Now

Luxury Villa 190 Next To Resort I Hot Tub I Sauna I Amazing Views I Best Price I Free Adventures Daily

190 Dream Catcher South, Winter Park, United States Show map

Offering a location 18 minutes' stroll from Amaze'n Mazes Colorado Amusement Center, Luxury Villa Oasis: Resort-Adjacent Retreat with Hot Tub & Complimentary Activities Winter Park gives access to… More

From US$ 518 Book Now

Downtown Wp Loft 101 I Large Hot Tub I Great Views I Activity Program

400 Baker Dr. #101, Winter Park, United States Show map

Luxe Loft Retreat: Hot Tub, Views & Activity Perks Villa Winter Park is just a 5-minute walk from The Foundry Cinema and Bowl, offering guests to unwind at a hot tub. Located 3.9 km from Fraser… More

From US$ 165 Book Now

Incredible Winter Park River Mansion With Endless Amenities - Must View

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

Situated nearly a 25-minute walk from Cozens Ranch House Museum, the 5-bedroom Incredible Winter Park River Mansion With Endless Amenities - Must View villa provides access to numerous tourist… More

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Walk To Dtwn: Fraser Retreat W/ Hot Tub & Views!

51 Kingfisher Pt, Winter Park, United States Show map

The 2-bedroom Walk To Dtwn: Fraser Retreat W/ Hot Tub & Views! Winter Park villa is located approximately a 10-minute drive from the outdoor sports store "Colorado Adventure Park" and provides a… More

From US$ 583 Book Now

Ski In Out Villa 464 I Private Hot Tub I Great Views I Outdoor Fireplace I Activity Program

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

Offering a Jacuzzi for a relaxing experience, Ski In Out Villa 464 I Private Hot Tub I Great Views I Outdoor Fireplace I Activity Program Winter Park is located 7 km from Cozens Ranch House Museum. More

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Winter Park Resort Home 1040 I Private Hot Tub I Great Views I Game Room I Discounted Attractions

1040 Arrow Trail, Winter Park, United States Show map

Boasting a Jacuzzi, the 5-bedroom Winter Park Resort Home 1040 I Private Hot Tub I Great Views I Game Room I Discounted Attractions is located only a few steps from Main Street and can accommodate 14… More

From US$ 1617 Book Now

Coziest Condo

210 Village Dr #15-33, Winter Park, United States Show map

With the capacity to host 6 guests, the 2-bedroom Coziest Condo Winter Park villa is located approximately 25 minutes on foot from such significant cultural landmarks as Cozens Ranch House Museum. More

From US$ 383 Book Now

Villa 306 Next To Wp Resort I Private Hot Tub I Great Views I Activity Program

306 Antler Way, Winter Park, United States Show map

Luxury Villa Resort: Hot Tub, Views & Free Activities Winter Park is located about a 25-minute walk from Coca Cola Tubing Hill At Winter Park and provides a Jacuzzi. This 3-bedroom holiday home hosts… More

From US$ 558 Book Now

Winter Park Cabin! Walk To Shuttle & Mtn Views

5 Mountain Flower Cir, Winter Park, United States Show map

Located just 0.7 km from the outdoor sports store "Colorado Adventure Park", the 3-bedroom Winter Park Cabin! Walk To Shuttle & Mtn Views boasts an outdoor swimming pool, a Jacuzzi for a relaxing… More

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Founders Pointe Winter Park Base Massive Hot Tub

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

Staying at Founders Pointe Studio 4471 | Steps To Gondola Winter Park villa, guests can visit Winter Park Resort, which is nearly a 20-minute stroll away. More

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Walk To Trails & Hideaway Park! Main Street Condo

301 Lions Gate Dr Unit 110, Winter Park, United States Show map

The 3-bedroom Walk To Trails & Hideaway Park! Main Street Condo Winter Park villa, located about a 5-minute walk from Vasquez Peak Wilderness, can host up to 8 guests. Offering a hot tub, the holiday… More

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78311 Us Hwy 40 Unit 6

78311 Us Hwy 40, Unit 6, Winter Park, United States Show map

The 2-bedroom 78311 Us Hwy 40 Unit 6 Villa Winter Park is nestled merely a 9-minute walk from Cozens Ranch House Museum and can accommodate up to 6 guests. Guests can enjoy snow skiing, hiking, and… More

From US$ 524 Book Now