Winter Park holiday lettings

We found 1,380 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 77 homes, 53 apartments and other holiday rentals in Winter Park that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a pool. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The lively area of Winter Park awaits your stay

Enjoy the live music and other features of Winter Park. Renowned for its university setting, shopping and gardens, this city welcomes all visitors. Universal Studios Florida and Universal Orlando Resort are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Winter Park

Are you searching for attractions to visit in the area? Venture out of your holiday home and experience everything that makes Winter Park a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Florida (11.6 mi / 18.7 km)
  • Universal Orlando Resort (11.7 mi / 18.9 km)
  • Walt Disney World® Resort (19.4 mi / 31.3 km)
  • The Wizarding World of Harry Potter™ (11.5 mi / 18.5 km)
  • Universal CityWalk (11.6 mi / 18.7 km)
  • Universal’s Islands of Adventure (12 mi / 19.3 km)

Exploring the natural landscape of Winter Park

Whether you're an active traveller or just want to take in the scenery, Winter Park is a great place to spend some time outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Harry P. Leu Gardens (2.3 mi / 3.8 km)
  • Loch Haven Park (2.6 mi / 4.1 km)
  • Lake Eola (4.4 mi / 7 km)
  • Lake Eola Park (4.4 mi / 7.1 km)
  • Red Bug Lake Park (4.6 mi / 7.4 km)
  • Cranes Roost Park (5.3 mi / 8.5 km)

Travelling to and around Winter Park

The nearest airport is in Orlando International Airport (MCO), located 11.8 mi (19 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Orlando, FL (SFB-Orlando Sanford Intl.), which is 13.4 mi (21.6 km) away.

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

Frequently asked questions

What is the best area to stay in Winter Park when booking a holiday rental?

Goldenrod is one of the most in-demand locations to book a holiday home in Winter Park. Settle in here and enjoy the relaxation and comfort that comes with having a whole place to yourself.

What is the most popular type of holiday rental accommodation in Winter Park?

Based on our research, houses are the most sought-after type of holiday rental in Winter Park. But as you know, everyone's idea of the perfect stay differs. Vrbo has holiday homes with every shape, size and budget in mind, and we'll help you find your ideal match.

How much does it cost to rent a holiday rental in Winter Park?

Season, property type and length of stay are some of the conditions that can determine the price of a holiday home. Simply enter your travel dates to find your ideal fit. From cosy chalets to expansive luxury villas, all Vrbo holiday rentals offer incredible value.

How much does it cost to rent a beach house in Winter Park?

Prices for beach houses in Winter Park may vary depending on the size and style of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and the number of guests to view your rental options and prices. From there you can use our filter tool to tailor your search by amenities, ratings, nearby activities and more.

Are there pet-friendly holiday rentals in Winter Park?

Pack a suitcase and a bone for your pooch because Winter Park has 44 stays that welcome pets with open arms. Let your furriest friend have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates then check the "Pets allowed" filter box.

Can I rent a house with a pool in Winter Park?

Dig out your swimwear and inflatable swan, because there are 20 houses with a private pool in Winter Park. Book a stay at one of these popular holiday rentals and let every day be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!

What are popular rental amenities in Winter Park?

A firepit, nearby museums and an electric car charging station head the list of most popular rental amenities in Winter Park. Whether you plan to go on your own, with your sweetheart or as a family, Vrbo will help you find a holiday rental that suits your tastes with all the features you need.

Are there large group holiday rentals in Winter Park?

Winter Park has two holiday rentals that can fit 10 or more guests. These stays come with enough space to enjoy good times with loved ones.

Are there holiday rentals in Winter Park that welcome kids?

Gather your whole family for the adventure of a lifetime in Winter Park at one of our 44 family-friendly holiday properties. Lots of these stays offer conveniences that are ideally suited to trips with youngsters, including kitchens, bunk beds and entertainment units. Just check the "Properties good for families" filter and pick out your favourite.

What are the top attractions for families in Winter Park?

Keep the kids amused at these top family-friendly attractions in Winter Park:

  • Orlando Science Centre
  • Church Street Station
  • Boardwalk Bowl Entertainment Centre

Are there one-bedroom holiday rentals in Winter Park?

Yes, there are 15 one-bedroom properties in Winter Park to pick from. A one-bedroom holiday property is a great option if it's just the two of you or if you're flying solo. Throw in more convenience, space and privacy than a hotel, and you've got the makings of an unforgettable getaway.

Can I find two-bedroom holiday rentals in Winter Park?

Gather your besties and relax in total privacy and comfort in one of the 14 two-bedroom holiday properties Winter Park has to offer.

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