Winter Park Vacation Rentals

Compare 699 available properties from 23 providers
Winter Park
Save up to 33%

Best vacation home deals in Winter Park

$309
from $254
-18%
House
4 2
Winter Park, Orange County, Florida, United States
Found on
HomeAway
$414
from $277
-33%
2100 ft² House
6 3
College Park, Orlando, Florida, United States
Found on
HomeAway
$223
from $184
-18%
700 ft² Apartment
2 1
Winter Park, Orange County, Florida, United States
Found on
HomeAway

Discover a vacation rental that meets your criteria among the 699 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 23 different providers.

Recommended vacation rentals in Winter Park

Rent a vacation accommodation in Winter Park: from $60 per night

$193
from $98
-49%
310 ft² Apartment
2 1
Winter Park, Orange County, Florida, United States
4.8
"Excellent" 8 reviews
Found on HomeAway
from $119
House
4 2
Winter Park, Orange County, Florida, United States
4.0
"Very good" 1 review
Found on HomeAway
from $177
950 ft² House
3 2
Winter Park, Orange County, Florida, United States
5.0
"Excellent" 9 reviews
Found on HomeAway
from $217
1000 ft² House
2 1
Winter Park, Orange County, Florida, United States
5.0
"Excellent" 23 reviews
Found on HomeAway
from $234
1400 ft² House
4 2
Winter Park, Orange County, Florida, United States
4.7
"Excellent" 9 reviews
Found on HomeAway
$309
from $254
-18%
House
4 2
Winter Park, Orange County, Florida, United States
4.8
"Excellent" 9 reviews
Found on HomeAway
from $193
1010 ft² House
4 2
Winter Park, Orange County, Florida, United States
5.0
"Excellent" 4 reviews
Found on HomeAway
$279
from $216
-22%
1500 ft² House
5 2
Winter Park, Orange County, Florida, United States
4.8
"Excellent" 27 reviews
Found on HomeAway
See all offers

  Vacation houses with pools

$130
from $70
-47%
House
2 1
Winter Park, Orange County, Florida, United States
4.7
"Excellent" 3 reviews
Found on HomeAway
$117
from $86
-27%
500 ft² House
4 1
Fern Park, Seminole County, Florida, United States
5.0
"Excellent" 14 reviews
Found on HomeAway
$414
from $277
-33%
2100 ft² House
6 3
College Park, Orlando, Florida, United States
4.7
"Excellent" 26 reviews
Found on HomeAway
from $229
1350 ft² House
4 2
Winter Park, Orange County, Florida, United States
4.7
"Excellent" 15 reviews
Found on HomeAway
See all offers

  Vacation homes with fishing spots nearby

from $248
2500 ft² House
6 2
Winter Park, Orange County, Florida, United States
5.0
"Excellent" 10 reviews
Found on HomeAway
from $290
House
6 3
Winter Park, Orange County, Florida, United States
4.9
"Excellent" 11 reviews
Found on HomeAway
from $359
1890 ft² House
8 3
Winter Park, Orange County, Florida, United States
5.0
"Excellent" 16 reviews
Found on HomeAway
from $175
1000 ft² House
5 2
Winter Park, Orange County, Florida, United States
4.8
"Excellent" 5 reviews
Found on HomeAway
See all offers

  Apartments with a balcony or patio

from $133
960 ft² Apartment
4 2
Altamonte Springs, Seminole County, Florida, United States
5.0
"Excellent" 5 reviews
Found on HomeAway
from $314
2000 ft² House
9 3
Winter Park, Orange County, Florida, United States
4.8
"Excellent" 79 reviews
Found on HomeAway
from $137
500 ft² Apartment
2 1
Northeast Orlando, Orlando, Florida, United States
4.9
"Excellent" 17 reviews
Found on HomeAway
from $117
280 ft² House
5 1
Orlando, Orange County, Florida, United States
4.3
"Outstanding" 20 reviews
Found on Booking.com
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Popular rental amenities in Winter Park

  • Kitchen (567)
  • Internet (538)
  • AC (531)
  • No smoking (530)
  • TV (519)
  • No pets (465)
  • Parking (453)
  • Washer (380)
  • Pool (367)
  • Dishwasher (228)
  • Microwave (185)
  • Grill (159)
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 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 July (7/28 - 8/4), where prices hit an average of $172 a night. On the other hand, in February you will find the cheapest prices (2/16 - 2/23). Prices this week are on average $140 a night.

Rental Availability Information in Winter Park

The availability graph shows the percentage of available rentals in Winter Park. It is in February that you will find the week with the least available rentals (2/9 - 2/16). People tend to travel less to Winter Park during a week in September (9/15 - 9/22) when only 17% of the rentals are booked.

The weather in Winter Park

72°
54°
75°
55°
79°
59°
84°
66°
88°
70°
90°
73°
91°
75°
91°
75°
90°
75°
84°
68°
77°
61°
77°
59°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Winter Park. July is the warmest month of the year in Winter Park with temperatures reaching a maximum average of 91°. On the contrary, the coolest month is January. It may rain 19 days in August while it typically rains only 6 days in November.

519 out of the 699 listed accommodations in Winter Park are house rentals. They account for two-thirds of the accommodation types in this destination (71.39%). In addition, house rentals there have an average cost of $272 per night as well as an average size of 1,560 ft². Moreover, these accommodations are a great choice for large groups, as most can welcome 9 people. Apartment rentals are the second most typical accommodation option in Winter Park. The average size of apartment rentals in Winter Park is 1,010 ft², and the average price is $170 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 699 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 250 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 Wimdu 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