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The 10 Best Vacation Homes in Winter Park, USA

Check out our selection of great vacation homes in Winter Park

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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The spacious holiday home with a balcony and mountain views features 2 bedrooms, a living room, a TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a hot tub. The accommodation offers a fireplace.

Size, location, cleanliness, decor, hot tub.

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9.3
Wonderful
6 reviews
Price from
$201.15
per night

Situated in Winter Park in the Colorado region, Ski In Ski Out Luxury Condo #4574 - Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily features a patio. Guests can benefit from a balcony and a children's playground. The holiday home features an American restaurant.

Great location. Wonderful natural light. Quiet and peaceful.

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9.2
Wonderful
11 reviews
Price from
$191.09
per night

Situated in Winter Park in the Colorado region, New Luxury Loft #3 - Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily features a patio. Boasting a 24-hour front desk, this property also provides guests with a children's playground. The holiday home features a restaurant serving American cuisine, as well as free WiFi throughout the property.

Free parking, pet friendly, hot tub, grill, kitchen, comfortable beds, location… everything!

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9.6
Exceptional
5 reviews
Price from
$191.09
per night

Kings Crossing Apartments offers accommodation in Winter Park. Among the facilities at this property are a lift and an ATM, along with free WiFi throughout the property. When staying at the holiday home, guests can use private entrance.

Proximity to the resort. Nice parking area. The size of the apartment was very nice.

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9.1
Wonderful
8 reviews
Price from
$146
per night

Located in Winter Park in the Colorado region, New Luxury Loft #404 - Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily has a patio. Among the facilities of this property are a restaurant, a 24-hour front desk and a lift, along with free WiFi throughout the property. The holiday home also offers facilities for disabled guests.

Location and place was very nice

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9.3
Wonderful
6 reviews
Price from
$191.09
per night

The spacious holiday home features 3 bedrooms, a flat-screen TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 4 bathrooms with a hot tub. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

It had everything that we needed, and I really liked having 4 bathrooms.

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9
Wonderful
7 reviews
Price from
$196
per night

Boasting accommodation with a patio, New Luxury Loft #17 With Huge Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily is located in Winter Park. Featuring a 24-hour front desk, this property also provides guests with a children's playground. Providing free WiFi throughout the property, the non-smoking holiday home has a fitness room.

great location, very clean and comfortable, very nice place

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10
Exceptional
6 reviews
Price from
$191.09
per night

Boasting accommodation with a patio, Slopeside Luxury Villa #126 Next To Resort With Steam Shower & Amazing Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily is located in Winter Park. Featuring a 24-hour front desk, this property also provides guests with a children's playground. Providing free WiFi throughout the property, the non-smoking holiday home has a fitness room.

It was beautiful, had lots of bedrooms and bathrooms, the view was gorgeous. Was a very relaxing vacation.

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9.2
Wonderful
9 reviews
Price from
$383.46
per night

The holiday home also features an infinity pool and a fitness room for guests to relax in. For guests with children, Luxury Villa #190 Next To Resort With Hot Tub, Sauna and Amazing Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily provides a children's playground. Skiing and cycling can be enjoyed nearby, while a bicycle rental service and ski storage space are also available on-site.

Absolutely everything about this property was a dream I wish I was still there!!

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9.4
Wonderful
5 reviews
Price from
$447.59
per night

Situated in Winter Park in the Colorado region, Luxury Condo #613 With Pool, Club House, Hot Tub & Great Views - 500 Dollars Of FREE Activities & Equipment Rentals Daily features a patio and mountain views. This property offers access to a balcony, free private parking and free WiFi. The holiday home features a children's playground and a 24-hour front desk.

The location is great! You can walk everywhere. The sledding hill is RIGHT across the street, which my kids loved. They also have a heated outdoor pool and hot tub, which is kind of fun in the middle of winter. Definately would recommend this place!

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8
Very Good
5 reviews
Price from
$201.15
per night

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.
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Vacation Homes That Guests Love in Winter Park

  • 10
    Scored 10
    Exceptional
    Rated exceptional
     · 2 reviews
    Great location. Well-maintained. Very clean. The condo was perfect for our family of four enjoying a few days on the mountain!
    Ashley
    Solo traveler
  • Avg. price/night: $123.13
    7.8
    Scored 7.8
    Good
    Rated good
     · 304 reviews
    The hotel is very cute and easy to get around. We booked a loft room which was unique to any other hotel experience I had! I loved the spiral staircase to the bed in the loft. The hotel was overall very clean but you can tell it’s an older hotel with some of the wear and tell and layers of dust in the just out of reach places. The staff was very friendly.
    A
    Andrea
    Young couple
  • Avg. price/night: $143.06
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 219 reviews
    spacious and very clean rooms, breakfast limited but adequate, very helpful staff.
    John
    Group
  • Avg. price/night: $140.37
    7.8
    Scored 7.8
    Good
    Rated good
     · 94 reviews
    Very clean, nice and friendly staff
    Daniel
    Solo traveler
  • 9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1 review
    The house was spacious and lovely! Very clean and plenty of room for our family to spread out. Loved the decks to hang out on in the morning light and sip some coffee. Kitchen was extremely well stocked with all kinds of gadgets to use. There were QUALITY cooking pans and utensils, such a delightful change from what we normally get at vacation homes. The neighborhood was quiet and peaceful. Thanks so much for hosting our stay.
    Piper
    Solo traveler
  • 7.9
    Scored 7.9
    Good
    Rated good
     · 17 reviews
    Great location, property very clean and really nicely arranged. There was a desk with 2 monitors, keyboard and computer mouse for work. Kitchen fully supplied with appliances, spices you may need while preparing the food.
    RysiaA
    Young couple