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Winter Park Vacation Rentals

Find 92 available offers from 14 partners
Winter Park
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Private room
Apartment
Distance to center
Max. 1 mi
Max. 2 mi
Max. 3 mi
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
Save up to 46%

Best Vacation Home Deals in Winter Park

Apartment Winter Park
Apr 30 - May 7
-46%
$118
$65 per night
Apartment ∙ 5 guests ∙ 1 bedroom
3.9
"Good" (7 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Details
Ventura Resort Rentals
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Apartment Winter Park
Apr 30 - May 7
-46%
$118
$65 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
3.8
"Good" (11 ratings)
Winter Park, Orange County, Florida, United States
Free cancellation
Details
Ventura Resort Rentals
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Aparthotel Winter Park
Apr 18 - Apr 25
-26%
$137
$101 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
4.6
"Outstanding" (1772 ratings)
Winter Park, Orange County, Florida, United States
Details
FindHotel
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Discover a vacation rental that meets your criteria among the 92 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 13 different providers.

Recommended Vacation Rentals in Winter Park

Find your perfect vacation rental in Winter Park: from $65 per night

House Winter Park
$106 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
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House Winter Park
$113 per night
House ∙ 8 guests ∙ 3 bedrooms
4.0
"Very good" (1 rating)
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
View deal
Apartment Winter Park
$135 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.0
"Very good" (3 ratings)
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
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Apartment Winter Park
$102 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
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House Winter Park
$103 per night
House ∙ 8 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
View deal
Apartment Winter Park
$106 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
View deal
Apartment Winter Park
$93 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.0
"Very good" (3 ratings)
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
View deal
Apartment Winter Park
$94 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (5 ratings)
Winter Park, Orange County, Florida, United States
Details
Ventura Resort Rentals
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Apartment Winter Park
$127 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
Details
HouseStay
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Vacation rentals and apartments with air conditioning

House Aircondition Winter Park
May 7 - May 14
$175 per night
House ∙ 7 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Winter Park, Orange County, Florida, United States
Free cancellation
Aircondition
Details
TripAdvisor
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Vacation rentals with Wi-Fi

House Internet Winter Park
Apr 30 - May 7
$176 per night
House ∙ 6 guests ∙ 5 bedrooms
Winter Park, Orange County, Florida, United States
Free cancellation
Internet
Details
TripAdvisor
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Aparthotel Internet Winter Park
Aug 17 - Aug 24
-28%
$159
$114 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
4.1
"Very good" (79 ratings)
Winter Park, Orange County, Florida, United States
Internet
Details
Sonder
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Aparthotel Internet Winter Park
Jan 25 - Feb 1
-52%
$221
$106 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Internet
Details
HomeToGo
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Apartments and vacation rentals with a kitchen

House Kitchen Winter Park
Jan 28 - Feb 4
$107 per night
House ∙ 6 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Kitchen
Details
TripAdvisor
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Aparthotel Kitchen Winter Park
Jul 2 - Jul 9
$119 per night
Aparthotel ∙ 6 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Kitchen
Details
HomeToGo
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Aparthotel Kitchen Winter Park
Feb 12 - Feb 19
$345 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Kitchen
Details
HomeToGo
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Popular Rental Amenities in Winter Park

  • Internet (64)
  • TV (55)
  • Air conditioning (47)
  • No smoking (35)
  • Yard (35)
  • No pets (32)
  • Balcony/Patio (20)
  • Pool (18)
  • Wheelchair access (14)
  • Microwave (13)
  • Parking (6)
  • Pet allowed (5)

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 like to end your days curled up by the fire or if you are a grill master as "grills" and "fireplaces" are not very popular amenities in Winter Park.

The Weather in Winter Park

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Min.
72°
54°
9 days 9
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75°
55°
7 days 7
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79°
59°
7 days 7
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84°
66°
8 days 8
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88°
70°
9 days 9
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90°
73°
17 days 17
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91°
75°
17 days 17
max.
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91°
75°
19 days 19
max.
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90°
75°
16 days 16
max.
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84°
68°
7 days 7
max.
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77°
61°
6 days 6
max.
Min.
77°
59°
8 days 8
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- 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.

7-Day Weather Forecast in Winter Park

Thu, 20 Jan
75°
57°

0%

9 h

6 mi/h

Fri, 21 Jan
75°
60°

0%

3 h

6 mi/h

Sat, 22 Jan
62°
57°

15%

0 h

12 mi/h

Sun, 23 Jan
62°
50°

10%

5 h

8 mi/h

Mon, 24 Jan
66°
44°

0%

8 h

5 mi/h

Tue, 25 Jan
75°
59°

15%

0 h

4 mi/h

Wed, 26 Jan
73°
60°

15%

5 h

8 mi/h

Accommodations for your vacation in Winter Park

70 out of the 92 listed accommodations in Winter Park are hotel rooms. They account for nearly all of the accommodation types in this destination (92.11%). In addition, hotel rooms there have an average cost of $299 per night as well as an average size of 310 ft². Moreover, these accommodations are a great choice for couples and small groups, as most can welcome 3 people. Private rooms are the second most typical accommodation option in Winter Park. The average size of private rooms in Winter Park is 500 ft², and the average price is $153 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 92 properties
Where to find the best food in Winter Park?

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.

What are the best places to discover the arts and culture of Winter Park?

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.

What are the best activities for families in Winter Park?

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.

Frequently Asked Questions

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

The price for Hotel rooms and Private rooms in Winter Park is $65 per night.

What amenities are most popular for vacation homes in Winter Park?

If you're looking to book a vacation rental in Winter Park, the most common amenities others search for are houses with internet, TVs, and yards.

How many vacation rentals are in Winter Park?

Discover 92 vacation rentals available to book in Winter Park.

Are pets allowed in vacation rentals in Winter Park?

Yes, there are 2 vacation homes in Winter Park that allow pets, with an average price of $338 per night.

What's the best time of year to travel to Winter Park ?

July and August are typically the warmest months in Winter Park with temperatures around 91 °F. January and February in Winter Park are the coldest, with 53 °F on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Winter Park TripAdvisor Vacation Rentals in Winter Park Vrbo Vacation Rentals in Winter Park Airbnb 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 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

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