Photo by Kayla Templin

Old Town Winter Park vacation rentals

We found 582 vacation rentals — enter your dates for availability

Select from 30 houses, 31 condos, and other vacation rentals to find the perfect place for your stay in Old Town Winter Park. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, such as WiFi and a hot tub. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Old Town Winter Park

Showing deals for:Aug 1 - Aug 8
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Frequently asked questions

What is the most popular type of vacation rental accommodation in Old Town Winter Park?
Condos are the most popular kind of vacation rental in Old Town Winter Park, according to our data. Even if you’ve got something else in mind, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect Old Town Winter Park pad.
How much does it cost to rent a vacation rental in Old Town Winter Park?
Season, property type and length of stay are some of the conditions that can determine the price of a vacation home. Simply click on your travel dates to find the ultimate escape. From cozy cabins to sprawling villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Old Town Winter Park?
Prices for beach houses in Old Town Winter Park vary depending on the style and size of the property and time of year you’re traveling. Simply enter your dates of travel into Vrbo and how many guests to see available options and prices. From there you can use our filter tool to refine your search results by ratings, amenities and more.
Are there pet-friendly vacation rentals in Old Town Winter Park?
Pack a suitcase and a bone for your beloved pooch because Old Town Winter Park has 48 properties that roll out the welcome mat to pets. Let your happy hound join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check our “Pets allowed” filter box.
Can I rent a house with a pool in Old Town Winter Park?
Pack your swimsuit and pool noodle, because there are 18 houses with a private pool in Old Town Winter Park. Book a stay at one of these superb vacation homes and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Old Town Winter Park?
When it comes to rental amenities that guests are on the lookout for in Old Town Winter Park, ski-in/ski-out facilities, tennis and a firepit rank highest. With Vrbo vacation rentals, there are choices to suit your taste and style, whether you’re planning to get away with relatives, friends or even pets.
Are there large group vacation rentals in Old Town Winter Park?
Old Town Winter Park has 25 vacation properties that can fit 10 or more people. These stays come with all the space you need to enjoy good times with friends and family.
Are there vacation rentals in Old Town Winter Park that welcome kids?
With 48 family-friendly vacation properties available in Old Town Winter Park, now is an awesome time to introduce your kids to the magic of travel. Simply check our “Properties good for families” filter box to discover stays packed with conveniences perfect for traveling families, like dining rooms, yards, entertainment units and bunk beds.
Are there one-bedroom vacation rentals in Old Town Winter Park?
Old Town Winter Park has four one-bedroom rentals on offer. Often positioned in prime areas due to their compact size, a one-bedroom vacation rental is perfect if you’re getting away with a buddy or your partner. And with home comforts such as laundry facilities and more privacy than a standard hotel, you’ll be able to chill out while enjoying this fantastic destination.
Can I find two-bedroom vacation rentals in Old Town Winter Park?
Old Town Winter Park has seven two-bedroom vacation properties to choose from. Book a vacation home with all the privacy and space you’re looking for at a price that won’t break the bank on Vrbo.
Are there vacation rentals with WiFi in Old Town Winter Park?
You’ll have a choice of 17 vacation rentals with WiFi in Old Town Winter Park. If you’d like to disconnect from the world on your escape, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Old Town Winter Park?
Select your dates and then use our filters to search for vacation rentals with ac in Old Town Winter Park on Vrbo. With five air-conditioned properties to choose from here, you can look forward to a cool and comfortable break.
How old do you have to be to rent a vacation rental in Old Town Winter Park?
The minimum required age is usually 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your chosen Old Town Winter Park vacation rental before booking your escape.
How long can I rent a vacation rental in Old Town Winter Park for?
The length of time you can book a vacation rental in Old Town Winter Park varies according to the property. Simply enter your preferred travel dates to display a list of options offering extended stays. With many creature comforts like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to get the perfect place to call your home away from home in Old Town Winter Park.
Does Vrbo offer discounts for vacation homes in Old Town Winter Park?
In Old Town Winter Park, you’ll find some fabulous bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re after a weekend getaway or a longer stay, we’ve got plenty of options that’ll suit your style.

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