Winter Park vacation rentals

We found 1,558 vacation rentals — enter your dates for availability

Discover a selection of 72 homes, 39 apartments, and other vacation rentals in Winter Park that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include a garden and WiFi. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

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Winter Park is warm enough to make your cares melt away

If the word "winter" conjures images of icy winds and smiling snowmen, think again. This city is where smart travelers flee the harshest winter climates for something a little more summery. Known for its chain of tree-lined lakes and colorful gardens, Winter Park has long been a retreat for families, older folks, and couples enjoying romantic honeymoons. These lucky visitors benefit from a surprisingly chic array of restaurants and classy boutiques, plus impressive art museums and historic homes. You can count on your Winter Park vacation rental being close to worldly attractions, but suffused with a get-away-from-it-all vibe.

A little city with big art, long history, and grand gardens

For a suburban city spread over a mere 10 square miles, Winter Park has an awfully swanky collection of cultural, historical, and natural attractions. Its Charles Hosmer Morse Museum of American Art is world-famous for its collection of Louis Comfort Tiffany pieces. The Hannibal Square Heritage Center is dedicated to the African Americans who lived and worked in the area in the 19th century. Plus, no matter where your Winter Park vacation rental lies, it'll be close to a botanical garden. The Mead Botanical Garden on Lake Sue and the Kraft Azalea Gardens on Lake Maitland are standouts.

Enjoy the sunny scene on foot, on wheels, or on the water

The easiest way to enjoy Winter Park is simply to step outside and start walking toward Park Avenue, a prime destination for excellent restaurants, upscale shopping, and cocktail bars with outdoor seating. Tired of walking? Keep the sightseeing going with a scenic boat tour through the lakes, or take a bike tour of historic homes and buildings. Of course, you can always head 30 minutes south to Walt Disney World if that's what the family is clamoring for, but Winter Park has a way of making anything other than its quaint southern charm seem unnecessary.

Enjoy the winter of your content in Winter Park

What's in a name? In this case, plenty. Maybe it's called Winter Park because you should park yourself here all winter. Temperatures range from the high 50s to the 70s on most days from November through February, and although prices are at a premium, the sunny skies might be worth it. Spring and fall are also special, especially if you're looking for a bargain on a Winter Park vacation rental. Just remember that rainy weather (and occasional hurricanes) can hit from June to November. Bring your rain gear and listen to local meteorologists.

Tropical trees and feathered friends abound in Winter Park

Winter Park's warm, watery climate is perfect for the oaks and moss-draped camphor trees that make you feel like you're on the edge of a wetland wilderness, even while strolling through the middle of town. Paddle a kayak, or take a boat tour through the city's many lakes and admire the banana trees as you keep an eye out for black anhingas and purple martins. This is an ideal destination for bird watchers. The Mead Botanical Garden has reported sightings of barred owls, Cooper's hawk, and the rare red-headed woodpecker.

Traveling to and around Winter Park

The nearest airport is in Orlando Intl. Airport (MCO), located 11.8 mi (19 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Orlando Sanford Intl. Airport (SFB), which is 13.4 mi (21.6 km) away.

If you prefer train travel, the main station is Winter Park Station.

Frequently asked questions

What is the best area to stay in Winter Park when booking a vacation rental?
Among the more popular locations to book a vacation home in Winter Park is Goldenrod. Discover your dream stay on Vrbo and experience this area like a local.
What is the most popular type of vacation rental accommodation in Winter Park?
Based on our research, apartments are the most sought-after vacation rental type in Winter Park. But as you’d expect, everyone’s idea of an epic trip isn’t going to be the same. Vrbo has vacation homes in a variety of shapes and sizes, and we’ll help you to find the perfect fit.
How much does it cost to rent a vacation rental in Winter Park?
The average price for a vacation rental in Winter Park depends on a number of factors, such as season, length of stay and property type. Whether you’re looking for a sprawling villa with a pool or a quaint cabin just enough for two, just enter your travel dates to see stays with exceptional value.
How much does it cost to rent a beach house in Winter Park?
When you travel and the size and style of the property will influence the cost of your beachside vacation rental. Put in your Winter Park travel dates to see all your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to pick the features and amenities you want in your vacation home.
Are there pet-friendly vacation rentals in Winter Park?
Pack a bone and a squeezy toy for the pup in your life because Winter Park has 91 properties that throw out the welcome mat to pets. Let your four-legged pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Winter Park?
Pack your swimsuit and inflatable lounger, because there are 46 houses with a private pool in Winter Park. Kick back at one of these sought-after vacation rentals and make every day a pool day. Simply enter your dates into Vrbo, then check the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Winter Park?
An electric car charging station, a garden and a nearby waterfront head the list of most popular rental amenities in Winter Park. Whether you plan to go alone, with your other half or as a family, Vrbo can help you find a vacation rental that fits your style with all the features you’ll enjoy.
Are there large group vacation rentals in Winter Park?
Winter Park has five vacation homes that can host 10 or more guests. These stays come with enough space to enjoy good times with your nearest and dearest.
Are there vacation rentals in Winter Park that welcome kids?
With 89 family-friendly vacation properties to pick from in Winter Park, now is a great time to introduce your kids to the thrills of travel. Check our “Properties good for families” filter to find stays loaded with amenities ideal for vacationing families, such as living rooms, patios, entertainment areas and bunk beds.
What are the top attractions for families in Winter Park?
There’s a ton of awesome things to do and see with the family in Winter Park, including:

  • Winter Park Country Club
  • Crealde School of Art
  • Winter Park Village

Are there one-bedroom vacation rentals in Winter Park?
You can pick from 26 one-bedroom rentals in Winter Park. Whether you’re searching for a cozy cottage or an upmarket condo, our one-bedroom rentals are great if you don’t require a lot of space. One of the main perks of having your own digs? You’ll never need to share your trip with strangers.
Can I find two-bedroom vacation rentals in Winter Park?
Take your pick of 33 two-bedroom rentals in Winter Park. Give the kids the second room or fill it with a couple of your best buddies. There’s space for whoever’s fortunate enough to be joining your journey.
Are there vacation rentals with WiFi in Winter Park?
Winter Park has 63 vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to catching up on social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Winter Park?
Winter Park has 89 vacation rentals where you’ll be able to relax in air-conditioned comfort. To find a stay on Vrbo with this amenity, enter your preferred travel dates and use the filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Winter Park?
The minimum age is normally 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your preferred Winter Park vacation home before you book.
How long can I rent a vacation rental in Winter Park for?
The amount of time you can stay in a Winter Park vacation rental for is down to each property. Just tap in your preferred travel dates to find options offering longer term stays. They have all the things you need to make your extended break more comfortable and convenient, like kitchens and air conditioning. Some Vrbo vacation rentals may also offer weekly or monthly discounted prices, so you can hang around longer for less.
Does Vrbo offer discounts for vacation homes in Winter Park?
Weekend retreat or a well-deserved long vacation, Vrbo has some exclusive deals and discounted options in Winter Park to suit your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever it is you’re after, you’ll find the ideal place to stay — without breaking the bank.

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