Photo by Kayla Templin

Old Town Winter Park holiday homes

We found 606 holiday rentals — enter your dates for availability

Select from 32 houses, 42 flats and other holiday rentals to find the perfect place for your stay in Old Town Winter Park. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a fireplace and garden. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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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 Old Town Winter Park?
The most sought-after types of holiday homes in Old Town Winter Park are condos. Searching for something different? Bookabach has many options to match our guests' requirements, so you'll see holiday properties in all shapes and sizes. The perfect fit is waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Old Town Winter Park?
The average price for a holiday home in Old Town Winter Park can vary depending on factors including length of stay, season and property type. Whether you're thinking about a sprawling villa with space for extended family or a quaint cottage for just you and your sweetheart, just enter your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Old Town Winter Park?
When you travel and the style and size of the property will influence the cost of your beachside holiday home. Type in your Old Town Winter Park travel dates to see your options on Bookabach. Did someone just say "hot tub"? Use the filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday homes in Old Town Winter Park?
Pack a travel bag and a bone for your pooch because Old Town Winter Park has 44 holiday homes that open their doors to pets. Let your four-legged friend have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Old Town Winter Park?
Tick the "pool" box in our filter tool and choose from 15 houses with private pools in Old Town Winter Park on Bookabach. Lazy soak or ball games and races? Free time is up to you when your Bookabach holiday home has its own swimming pool.
What are popular home amenities in Old Town Winter Park?
A nearby river, mountain views and a nearby waterfront are rated the most popular home amenities in Old Town Winter Park. Whether you're travelling alone, with your other half or a group of best friends, Bookabach can help you find a holiday home that matches your tastes with all the features you're looking for.
Are there large group holiday homes in Old Town Winter Park?
With 21 holiday homes that can host 10 or more people in Old Town Winter Park, you don't have to keep your invite list short. From extended family holidays to events like Christmas and birthday parties, Bookabach will help you find a large group home that fits the occasion.
Are there holiday homes in Old Town Winter Park that welcome kids?
Old Town Winter Park has 44 family-friendly holiday homes. And discovering a stay that welcomes kids is a breeze with Bookabach's "Properties good for families" filter. As well as having the whole place to yourselves, you'll enjoy access to perks and conveniences such as dining rooms, kitchens and private pools.
What are the top attractions for families in Old Town Winter Park?
You'll find lots of amazing things to see and do with the family in Old Town Winter Park, including:

  • Amazen Maze Winter Park
  • Moffat Tunnel West Portal
  • Saint Marys Glacier

Are there one-bedroom holiday homes in Old Town Winter Park?
Yes, you'll find three one-bedroom properties in Old Town Winter Park to select from. A one-bedroom holiday home is an excellent option if it's only you and your partner or if you're holidaying alone. Add in more privacy, space and convenience compared to a standard hotel, and you've got yourself a memorable trip.
Can I find two-bedroom holiday homes in Old Town Winter Park?
Take your pick of six two-bedroom homes in Old Town Winter Park. Settle the kids into the second room or fill it with a couple of your besties. There's enough space for whoever's lucky enough to be joining your adventure.
Are there holiday homes with WiFi in Old Town Winter Park?
Whether you want to keep up with the headlines, make a video call or surf social media, there are 16 holiday homes with WiFi in Old Town Winter Park. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Old Town Winter Park?
Old Town Winter Park has five holiday homes where you can kick back in air-conditioned comfort. To locate a property on Bookabach that comes with this perk, choose your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Old Town Winter Park?
The minimum age permitted can vary across properties on Bookabach, so double-check the rules of the holiday home in Old Town Winter Park you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Old Town Winter Park for?
The length of time you can rent a holiday home in Old Town Winter Park is up to the property. Simply enter your preferred dates to look at a list of options offering extended stays. With a range of amenities such as kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to get the perfect place to call your home away from home in Old Town Winter Park.

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