Discover a selection of 500 vacation rentals in Winter Park, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $105 per night, and houses and condos are popular options for a stay in Winter Park. Either way, you'll find a rental for everyone's needs.
Destination guide

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.

Things to do

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.

Natural features

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.

How to get there

Transportation to and around Winter Park

The nearest airport is in Orlando, FL (MCO-Orlando Intl.), located 12 mi (19.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Orlando, FL (SFB-Orlando Sanford Intl.), which is 12.7 mi (20.5 km) away.

If you're traveling by train, you can make your way to Winter Park Station.

How many vacation rentals are available around Winter Park, FL?

Our 2020 property listings offer a large selection of 571 vacation rentals around Winter Park. From 300 house rentals to 188 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Winter Park?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winter Park:

  • Bahama Bay: 619 vacation rentals
  • Historic Downtown Kissimmee: 265 vacation rentals
  • Lindfields: 2,524 vacation rentals
  • Northeast Orlando: 141 vacation rentals
  • Sunset Lakes: 4,898 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Winter Park?

Vrbo offers a large selection of vacation rentals near lovely places in Winter Park. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Winter Park Village: 2,890 vacation rentals
  • Winter Park Station: 2,936 vacation rentals
  • Full Sail University: 2,246 vacation rentals
  • Rollins College: 3,511 vacation rentals
  • Casa Feliz Historic Home Museum: 2,501 vacation rentals

But there are many other points of interest around Winter Park listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Winter Park?

Yes, of course. Vrbo has 300 Houses in Winter Park. Our other popular types of vacation rentals in Winter Park include:

  • Condos/Apartments: 188 rentals available
  • Villas: 14 rentals available
  • Townhouses: 10 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Studios and more.

Can I find a vacation rental with pool in Winter Park?

Yes, you can select your preferred vacation rental with pool among our 304 vacation rentals with pool available in Winter Park. Please use our search bar to access the selection of vacation rentals available.

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