Winter Park Vacation Rentals

Compare 211 available properties from 18 providers
Winter Park
Anytime
2 guests
Save up to 22%

Best Vacation Home Deals in Winter Park

-22%
e.g. 9/28 - 10/5
House ∙ 7 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $235 $299
Vrbo
4.8
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-20%
e.g. 11/23 - 11/30
Villa ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $338 $422
RedAwning
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Discover a vacation rental that meets your criteria among the 211 beautiful accommodations from numerous partner websites in Winter Park. HomeToGo immediately features the best offers by comparing all of the listed vacation rentals in Winter Park from 18 different providers.

Recommended Vacation Rentals in Winter Park

Find your perfect vacation rental in Winter Park: from $26 per night

House ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $217
Vrbo
5.0
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House ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $175
Vrbo
4.8
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House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $254
Vrbo
4.7
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House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $305
Vrbo
5.0
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House ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $269
Vrbo
4.8
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Apartment ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $93
Airbnb
5.0
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House ∙ 5 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $77
Vrbo
5.0
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Apartment ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $71
Airbnb
4.8
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House ∙ 4 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $75
Airbnb
5.0
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Vacation Houses With Pools

Pool
Apartment ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $225
Vrbo
4.9
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Pool
House ∙ 10 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $101
Airbnb
4.4
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Pool
Apartment ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $144
Airbnb
5.0
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $362
Vrbo
5.0
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Pet-friendly
Apartment ∙ 5 guests
Winter Park, Orange County, Florida, United States
from $48
Airbnb
4.0
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Pet-friendly
Apartment ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $133
Airbnb
5.0
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $285
Vrbo
4.9
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Fireplace
House ∙ 9 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $359
Vrbo
4.8
View deal
Fireplace
Private room ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $49
Airbnb
4.8
View deal
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Popular Rental Amenities in Winter Park

  • Internet (205)
  • AC (205)
  • Kitchen (198)
  • TV (195)
  • Washer (177)
  • Microwave (121)
  • Dishwasher (94)
  • Yard (79)
  • Pool (75)
  • Grill (53)
  • Pet allowed (52)
  • Fireplace (42)
Filters are available to help you tailor your search and find a great vacation rental in Winter Park. Winter Park is the perfect destination to book a property if you can't imagine a vacation without internet or you want to tune out with some TV time, as the most frequently offered features are "internet" and "TVs." Not as many rentals in Winter Park are available if you plan to go fishing or if you like to end your days curled up by the fire as "fireplaces" and "fishing" are not very popular amenities in Winter Park.

The Weather in Winter Park

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- Rainy days

Check out the climate diagram for Winter Park. July is the warmest month of the year in Winter Park with temperatures reaching a maximum average of 91°. No heat wave is expected in January, where minimum average temperatures usally hit a 53° low. The rainiest month is August while the driest month is November.

Accommodations in Winter Park

89 out of the 211 listed accommodations in Winter Park are house rentals. They account for one-third of the accommodation types in this destination (38.53%). In addition, house rentals there have an average cost of $202 per night as well as an average size of 2,120 ft². Moreover, these accommodations are a great choice for medium-sized groups and families, as most can welcome 5 people. Private rooms are the second most typical accommodation option in Winter Park. The average size of private rooms in Winter Park is 1,090 ft², and the average price is $72 per night.

Rent a condo, or vacation home in Winter Park, on Orlando's doorstep

Winter Park, Florida offers beautiful vacation homes in the greater Orlando area. The most common of these are fully equipped condos with decks, gardens, and all the amenities you could ask for. There are also lavish villas available, near the sea or within the city center. Another option for your upcoming vacation are expansive vacation homes with multiple bedrooms, bathrooms, and backyards.

Show all 211 properties
Food & Drinks

Fine dining and cheap local eateries

Look no further than the scenic Park Avenue district to be spoiled for choice when it comes to dining. One of the most highly reviewed restaurants in the Winter Park area remains Hillstone Restaurant. Their rotisserie chicken is particularly appealing, as is their plethora of appetizer options. Luma on Park is another fine choice for a seasonally-based menu with fine wines. If you are looking for a great steakhouse, be sure to visit Fleming's Prime Steakhouse & Wine Bar. One of the best burger joints in Winter Park is BurgerFi. Other spots of interest include the Black Bean Deli, Toasted, and the Dandelion Communitea Cafe.

Art & Culture

Winter Park: historic and interesting sites

The Charles Hosmer Morse Museum of American Art is full of timely pieces both classic and modern. To encounter art outdoors, check out the Albin Polasek Museum & Sculpture Gardens. Cornell Fine Arts Museum offers more sophisticated art to enjoy. If you want to be immersed in Winter Park's history and culture, stop by the Winter Park Historical Museum, Casa Feliz Historic Home Museum, and the Hannibal Square Heritage Center.

Family Activities

Tons of fun for families, too

Kids will love the Saturday Farmer's Market in Winter Park, where you can buy vegetables directly from growers, or eat some freshly-popped popcorn. Right on Orlando's doorstep, Winter Park is also within reach of Orlando's Airheads Trampoline Arena, as well as the world-famous DIsney World. Another popular destination for families is the Petting Farm at Green Meadows Farm.

We compare more than 600 providers, including:

Booking.com Vacation Rentals in Winter Park Vrbo Vacation Rentals in Winter Park HomeAway Vacation Rentals in Winter Park Airbnb Vacation Rentals in Winter Park TripAdvisor Vacation Rentals in Winter Park VacationRentals.com Vacation Rentals in Winter Park HouseTrip Vacation Rentals in Winter Park FlipKey Vacation Rentals in Winter Park 9flats.com Vacation Rentals in Winter Park VaycayHero Vacation Rentals in Winter Park PerfectPlaces.com Vacation Rentals in Winter Park Homestay.com Vacation Rentals in Winter Park Only-apartments Vacation Rentals in Winter Park Interhome Vacation Rentals in Winter Park Bedycasa Vacation Rentals in Winter Park Novasol Vacation Rentals in Winter Park HomeEscape Vacation Rentals in Winter Park

Vacation Destinations Near Winter Park

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