Winter Park holiday rentals

We found 562 holiday rentals — enter your dates for availability

Discover a selection of 10 homes, 15 cabins and other holiday rentals in Winter Park that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winter Park

Showing deals for:17 Apr - 24 Apr

Image gallery for SPACIOUS MTN CHALET - Upscale 4 bedrooms (sleeps 12), Hot Tub, ideal location!

The 'Great Room,' where all the action happens! The perfect gathering place.
9.2 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)

SPACIOUS MTN CHALET - Upscale 4 bedrooms (sleeps 12), Hot Tub, ideal location!

Big Bear Lake

6% off
Price is AU$9,769
for 7 nights, 1 cabin
AU$1,396 per night
includes taxes & fees
SPACIOUS MTN CHALET - Upscale 4 bedrooms (sleeps 12), Hot Tub, ideal location!

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Winter Park?
According to our research, houses are the most sought-after holiday home type in Winter Park. But that goes without saying, everyone's idea of an epic trip isn't going to be the same. Stayz has holiday homes of all shapes, sizes and budgets, and we'll help you to find your ideal match.
How much does it cost to rent a holiday home in Winter Park?
The average price for a holiday home in Winter Park is based on a number of factors, such as season, length of stay and property type. Whether you prefer a sprawling villa with space for extended family or a comfy cabin for you and your other half, just add your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Winter Park?
When you travel and the style and size of the property will help determine the cost of your beachside holiday home. Type in your Winter Park travel dates to view your available options on Stayz. Did someone just say "private pool"? Use the filters to choose the features and amenities you want.
Are there pet-friendly holiday homes in Winter Park?
Yes. You can choose from 16 holiday homes that cater to pets in Winter Park. Some of our pet-friendly holiday homes even come with an outdoor space for your fur child to play in, complimentary treats, special dog beds and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect pad on Stayz.
Can I rent a house with a pool in Winter Park?
Add another level of fun to your getaway by booking your group into one of the 10 houses with a private pool in Winter Park. Use our handy search filter to find the kind of property you want on Stayz, and then spend your days frolicking in a swimming pool that's only for you.
What are popular home amenities in Winter Park?
A fireplace, ski-in/ski-out facilities and mountain views are rated the most popular home amenities in Winter Park. Whether you plan to travel by yourself, with your spouse or as a family group, Stayz can help you find a holiday home that fits your style with all the options you need.
Are there large group holiday homes in Winter Park?
Pick from 10 holiday homes in Winter Park that can accommodate a group of 10 or more guests. Whether you're organising a trip with the family or an event like a party, there's enough room to get your group together under the same roof.
Are there holiday homes in Winter Park that welcome kids?
With 16 family-friendly holiday properties available in Winter Park, now is an awesome time to introduce the kiddos to the wonders of travel. Just click on our "Properties good for families" filter to view stays that feature conveniences perfect for families on the move, such as full kitchens, pools, bunk beds and hot tubs.
What are the top attractions for families in Winter Park?
Keep your kids busy at these fantastic family-friendly attractions in Winter Park:

  • Alpine Slide at Magic Mountain
  • Big Bear Alpine Zoo
  • Bowling Barn

Are there holiday homes with WiFi in Winter Park?
Whether you'd like to keep up with the latest news, make a video call or surf social media, there are six holiday homes with WiFi in Winter Park. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How old do you have to be to rent a holiday home in Winter Park?
The minimum required age is generally 16, 18 or 21. It can vary from one property to another on Stayz, so check the rules of your chosen Winter Park holiday home before booking your stay.
How long can I rent a holiday home in Winter Park for?
It's up to the Winter Park property. To see a list of options offering extended stays, simply type your dates and number of guests into Stayz's search page. Enjoy having the property to yourself, along with home comforts such as a fully-equipped kitchen, air conditioning and an outdoor space to play in. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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