Winter Park Vacation Rentals - HomeToGo base64Hash Winter Park Vacation Rentals - HomeToGo

Winter Park Vacation Rentals

Find 5,252 available home rentals from 15 partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Cabin
    • Lodge
    • House

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • WiFi
    • Jacuzzi
    • Kitchen
    • Air conditioning
    • Washing machine
    • TV
    • Fireplace
    • Parking
    • Balcony/patio
    • Dishwasher
    • Microwave
    • Yard
    • Sauna
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Winter Park

Find your perfect vacation rental in Winter Park from just $169 per night!

Condo Winter Park
Condo ∙ 10 guests ∙ 3 bedrooms

196 m² Condo

Winter Park, Grand County, Colorado, United States
from $450
per night
Very good(17 ratings)
from $450
per night
View deal
House Winter Park
House ∙ 16 guests ∙ 6 bedrooms

House

Winter Park, Grand County, Colorado, United States
from $673
per night
Outstanding(90 ratings)
from $673
per night
View deal
House Winter Park
House ∙ 14 guests ∙ 5 bedrooms

214 m² House

Winter Park, Grand County, Colorado, United States
from $715
per night
Outstanding(35 ratings)
from $715
per night
View deal
House Winter Park
House ∙ 13 guests ∙ 4 bedrooms

362 m² House

Winter Park, Grand County, Colorado, United States
from $543
per night
Outstanding(10 ratings)
from $543
per night
View deal
House Winter Park
House ∙ 16 guests ∙ 4 bedrooms

House

Winter Park, Grand County, Colorado, United States
from $540
per night
Outstanding(88 ratings)
from $540
per night
View deal
House Winter Park
House ∙ 18 guests ∙ 4 bedrooms

277 m² House

Winter Park, Grand County, Colorado, United States
from $741
per night
Excellent(19 ratings)
from $741
per night
View deal
House Winter Park
House ∙ 11 guests ∙ 4 bedrooms

251 m² House

Winter Park, Grand County, Colorado, United States
from $637
per night
Outstanding(89 ratings)
from $637
per night
View deal
House Winter Park
House ∙ 16 guests ∙ 4 bedrooms

186 m² House

Winter Park, Grand County, Colorado, United States
from $692
per night
from $692
per night
View deal
House Winter Park
House ∙ 16 guests ∙ 6 bedrooms

297 m² House

Winter Park, Grand County, Colorado, United States
from $883
per night
Outstanding(166 ratings)
from $883
per night
View deal
House Winter Park
House ∙ 16 guests ∙ 4 bedrooms

House

Winter Park, Grand County, Colorado, United States
from $764
per night
Outstanding(29 ratings)
from $764
per night
View deal
House Winter Park
House ∙ 9 guests ∙ 3 bedrooms

142 m² House

Winter Park, Grand County, Colorado, United States
from $305
per night
Excellent(30 ratings)
from $305
per night
View deal
House Winter Park
House ∙ 12 guests ∙ 4 bedrooms

232 m² House

Winter Park, Grand County, Colorado, United States
from $613
per night
Outstanding(29 ratings)
from $613
per night
View deal
House Winter Park
House ∙ 12 guests ∙ 4 bedrooms

178 m² House

Winter Park, Grand County, Colorado, United States
from $380
per night
Outstanding(67 ratings)
from $380
per night
View deal
House Winter Park
House ∙ 14 guests ∙ 5 bedrooms

304 m² House

Winter Park, Grand County, Colorado, United States
from $583
per night
Outstanding(100 ratings)
from $583
per night
View deal
House Winter Park
House ∙ 10 guests ∙ 4 bedrooms

204 m² House

Winter Park, Grand County, Colorado, United States
from $484
per night
Outstanding(12 ratings)
from $484
per night
View deal

Vacation rentals and apartments with air conditioning

House Winter Park
from $331 per night
House ∙ 8 guests ∙ 2 bedrooms

125 m² House

5.0
Outstanding(79 ratings)
Winter Park, Grand County, Colorado, United States
Air conditioning
View deal
Chalet Winter Park
from $777 per night
Chalet ∙ 8 guests ∙ 4 bedrooms

279 m² Chalet

5.0
Outstanding(1 rating)
Winter Park, Grand County, Colorado, United States
Air conditioning
View deal
Cabin Winter Park
from $347 per night
Cabin ∙ 10 guests ∙ 3 bedrooms

167 m² Cabin

4.8
Outstanding(4 ratings)
Winter Park, Grand County, Colorado, United States
Air conditioning
View deal
See all offers

Apartments with a balcony or patio

Accommodation Winter Park
from $1,330 per night
Accommodation ∙ 14 guests ∙ 5 bedrooms

581 m² Accommodation

5.0
Outstanding(20 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House Winter Park
from $440 per night
8 guests ∙ 3 bedrooms

House

4.8
Outstanding(52 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House Winter Park
from $1,079 per night
House ∙ 19 guests ∙ 5 bedrooms

398 m² House

4.9
Outstanding(62 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a fireplace

Apartment Winter Park
from $470 per night
Apartment ∙ 10 guests ∙ 3 bedrooms

195 m² Apartment

4.2
Very good(17 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
Condo Winter Park
from $421 per night
Condo ∙ 6 guests ∙ 2 bedrooms

156 m² Condo

4.6
Excellent(30 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
House Winter Park
from $331 per night
House ∙ 8 guests ∙ 2 bedrooms

179 m² House

4.9
Outstanding(32 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
See all offers

Budget-friendly Rentals in Winter Park

Find Fantastic yet Inexpensive Rentals

Cabin Winter Park
from $294 per night
Cabin ∙ 8 guests ∙ 2 bedrooms

132 m² Cabin

4.6
Excellent(86 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Cabin Winter Park
from $613 per night
Cabin ∙ 12 guests ∙ 5 bedrooms

204 m² Cabin

5.0
Outstanding(38 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Condo Winter Park
from $452 per night
Condo ∙ 10 guests ∙ 3 bedrooms

258 m² Condo

5.0
Outstanding(67 ratings)
Winter Park, Grand County, Colorado, United States
View deal

Top-Rated Offers and Accommodations in Winter Park

Book Vacation Rentals with the Highest User Rating

House Winter Park
from $538 per night
House ∙ 9 guests ∙ 3 bedrooms

191 m² House

4.9
Outstanding(113 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
from $293 per night
House ∙ 10 guests ∙ 3 bedrooms

187 m² House

4.9
Outstanding(81 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
from $445 per night
House ∙ 12 guests ∙ 4 bedrooms

229 m² House

4.9
Outstanding(79 ratings)
Winter Park, Grand County, Colorado, United States
View deal

Customer ratings and reviews

How are reviews collected?
Jane K.
Guest verified by HomeToGo

Absolutely wonderful. New, convenient, and beautifully appointed with new, clean appliances, and plenty of sunshine. Hot tub and fire pit make for a nice social gathering spot. Very quiet. Loved the Nordic ski and hiking available right outside our door!

Reviewed on 3/7/2024 | Group
House Winter Park
from $430 per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Izabela P.
Guest verified by HomeToGo

Difficulties with parking (QR code did not work, after 4 days our bill was close to 400,00 instead 76 dollars). No towels for hot tub. In the shower, no shower gel.

Reviewed on 1/31/2024 | Couple
Condo Winter Park
from $204 per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.3
Very good(48 ratings)
Winter Park, Grand County, Colorado, United States
View deal

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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Winter Park

  • Pool (1,857)
  • Pet-friendly (817)
  • WiFi (4,823)
  • Jacuzzi (2,896)
  • Kitchen (5,015)
  • Air conditioning (432)
  • Washing machine (3,584)
  • TV (4,769)
  • Fireplace (4,569)
  • Parking (1,537)
  • Balcony/patio (1,459)
  • Grill (2,056)

Winter Park is a good vacation destination if you want an accommodation with a pool, as 35% of the vacation rentals there have one. Additionally, more Condo have pools than any other accommodation type. They are a great choice if you go in a group of 6, as that is the number of people they can welcome on average. If you would ideally like to be close to the water, one-third of the vacation homes including a pool are situated within 2 kilometres of the waterfront.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 5,252 rentals
💳 Possible discounts up to 12%
🌙 Nightly prices starting at $169
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 797 homes
🏊 Vacation rentals with pools 1,816 homes
3 reviews
Winter Park vacation rentals have an average rating of 4.3/5 on 3 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Winter Park?

At the moment, there are 5,252 vacation homes from 14 different providers in Winter Park.

What are the most popular vacation home amenities in Winter Park?

When looking to book a vacation home in Winter Park, the most requested amenities include Pool, Pets allowed, and Internet.

Are there pet-friendly vacation rentals in Winter Park?

Yes, there are 797 pet-friendly vacation rentals in Winter Park, with an average nightly price of $658.

What's the best month to book a vacation rental in Winter Park?

The warmest time of year in Winter Park is July and June, with the nightly price of a vacation home starting at $169.

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