Winter Park Vacation Rentals

Compare 637 available properties from 30 providers
Winter Park
Save up to 41%

Best Vacation Home Deals in Winter Park

-17%
e.g. 2/2 - 2/9
House ∙ 2 guests ∙ 1 bedroom
Baldwin Park, Orlando, Florida, United States
from $95 $115
9flats.com
5.0
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-34%
e.g. 12/1 - 12/8
House ∙ 2 guests ∙ 4 bedrooms
Fairview Shores, Orange County, Florida, United States
from $125 $189
EveryStay
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-41%
e.g. 12/1 - 12/8
Condo ∙ 7 guests ∙ 3 bedrooms
Lake Davis/Greenwood, Orange County, Florida, United States
from $173 $292
Onefinestay
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Discover a vacation rental that meets your criteria among the 637 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 30 different providers.

Recommended Vacation Rentals in Winter Park

Rent a vacation accommodation in Winter Park: from $32 per night

House ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $146
HomeAway
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $119
HomeAway
4.7
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House ∙ 5 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $258
VRBO
5.0
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House ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $99
VRBO
4.7
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House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $151
HomeAway
4.5
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House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $201
VRBO
4.9
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House ∙ 4 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $105
VRBO
5.0
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House ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $216
VRBO
4.8
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Apartment ∙ 2 guests ∙ 1 bedroom
Fairview Shores, Orange County, Florida, United States
from $116
VRBO
4.9
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 6 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $249
VRBO
4.7
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Fishing
House ∙ 3 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $147
VRBO
5.0
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Fishing
House ∙ 5 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $176
VRBO
4.7
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Vacation Houses With Pools

Pool
Apartment ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
from $152
VRBO
4.9
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Pool
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $229
VRBO
4.7
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Pool
House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $390
HomeAway
4.8
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
from $194
VRBO
5.0
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Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
from $362
VRBO
5.0
View deal
Fireplace
House ∙ 2 guests ∙ 1 bedroom
Casselberry, Seminole County, Florida, United States
from $85
HomeAway
4.8
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Popular Rental Amenities in Winter Park

  • Kitchen (571)
  • AC (537)
  • Internet (534)
  • TV (531)
  • No smoking (521)
  • No pets (440)
  • Parking (416)
  • Washer (394)
  • Pool (328)
  • Dishwasher (274)
  • Microwave (245)
  • Grill (170)
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.

Price and Availability Index in Winter Park

Vacation Rental Price Information in Winter Park

This graph displays average prices of the vacation rentals and holiday apartments located in Winter Park. The most expensive week of the next 12 months is in December (12/15 - 12/22), where prices hit an average of $182 a night. On the other hand, in September you will find the cheapest prices (9/28 - 10/5). Prices this week are on average $149 a night.

Rental Availability Information in Winter Park

The availability graph shows the percentage of available rentals in Winter Park. It is in December that you will find the week with the least available rentals (12/22 - 12/29). People tend to travel less to Winter Park during a week in April (4/27 - 5/4) when only 15% of the rentals are booked.

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 July while the driest month is November.

Accommodations in Winter Park

489 out of the 637 listed accommodations in Winter Park are house rentals. They account for many of the accommodation types in this destination (64.6%). In addition, house rentals there have an average cost of $292 per night as well as an average size of 1,700 ft². Moreover, these accommodations are a great choice for large groups, as most can welcome 9 people. Hotel rooms are the second most typical accommodation option in Winter Park. The average size of hotel rooms in Winter Park is 360 ft², and the average price is $142 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 637 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 300 providers, including:

Booking.com Vacation Rentals in Winter Park VRBO Vacation Rentals in Winter Park HomeAway 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