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Winter Park Vacation Rentals

Find 160 available offers from 5 partners
Winter Park
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Choose the perfect vacation rental

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

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.

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Save up to 31%

Best Vacation Home Deals in Winter Park

House Winter Park
Feb 11 - Feb 18
-28%
$180
$130 per night
House ∙ 6 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
Jan 21 - Jan 28
-28%
$277
$200 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (30 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
Jun 17 - Jun 24
-31%
$119
$83 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Winter Park, Orange County, Florida, United States
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Discover a vacation rental that meets your criteria among the 160 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 5 different providers.

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Top-Rated Rentals and Accommodations in Winter Park

House Winter Park
Jan 21 - Jan 28
$373 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
"Excellent" (100 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
Dec 29 - Jan 5
$357 per night
Condo ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (39 ratings)
Winter Park, Orange County, Florida, United States
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Cottage Winter Park
Jan 7 - Jan 14
$208 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (33 ratings)
Winter Park, Orange County, Florida, United States
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Recommended Vacation Rentals in Winter Park

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

House Winter Park
Jan 21 - Jan 28
$373 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
"Excellent" (100 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
Mar 11 - Mar 18
$200 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
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Cottage Winter Park
Jan 7 - Jan 14
$208 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (33 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
Mar 25 - Apr 1
$357 per night
Condo ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (39 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Feb 25 - Mar 4
$140 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Jan 21 - Jan 28
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
Jul 22 - Jul 29
$147 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
"Outstanding" (95 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Feb 11 - Feb 18
-28%
$180
$130 per night
House ∙ 6 guests ∙ 2 bedrooms
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Jan 21 - Jan 28
$120 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Winter Park

Apartment Winter Park
Jan 21 - Jan 28
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
Mar 11 - Mar 18
$200 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
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House Winter Park
May 27 - Jun 3
$245 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
"Excellent" (8 ratings)
Winter Park, Orange County, Florida, United States
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Winter Park accommodation with high-speed internet.

House Internet Winter Park
Jan 21 - Jan 28
$373 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
"Excellent" (100 ratings)
Winter Park, Orange County, Florida, United States
Internet
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House Internet Winter Park
Mar 11 - Mar 18
$200 per night
House ∙ 8 guests ∙ 4 bedrooms
Winter Park, Orange County, Florida, United States
Internet
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Cottage Internet Winter Park
Jan 7 - Jan 14
$208 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (33 ratings)
Winter Park, Orange County, Florida, United States
Internet
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Winter Park and book a vacation rental with air conditioning.

Apartment Aircondition Winter Park
Feb 25 - Mar 4
$140 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Winter Park, Orange County, Florida, United States
Aircondition
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Apartment Aircondition Winter Park
Jan 21 - Jan 28
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Winter Park, Orange County, Florida, United States
Aircondition
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House Aircondition Winter Park
Jul 22 - Jul 29
$147 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
"Outstanding" (95 ratings)
Winter Park, Orange County, Florida, United States
Aircondition
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Winter Park rental with full kitchen.

House Kitchen Winter Park
Jan 21 - Jan 28
$317 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
"Excellent" (113 ratings)
Winter Park, Orange County, Florida, United States
Kitchen
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Apartment Kitchen Winter Park
Jan 7 - Jan 14
$180 per night
Apartment ∙ 14 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Kitchen
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Condo Kitchen Winter Park
Jan 21 - Jan 28
$125 per night
Condo ∙ 4 guests ∙ 1 bedroom
Winter Park, Orange County, Florida, United States
Kitchen
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Popular Rental Amenities in Winter Park

  • Internet (146)
  • Air conditioning (146)
  • TV (144)
  • No smoking (123)
  • Kitchen (91)
  • Microwave (91)
  • Yard (87)
  • No pets (82)
  • Washer (68)
  • Dishwasher (63)
  • Pool (59)
  • Pet allowed (46)

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 never miss an episode of your favorite show, as the most frequently offered features are "Internet" and "TV." Not as many rentals in Winter Park are available if you like to end your days curled up by the fire or if you want a rental with a balcony or a patio as "Balcony/Patio" and "Fireplace" are not very popular amenities in Winter Park.

The Weather in Winter Park

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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
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91°
75°
19 days 19
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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.
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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 54° low. The rainiest month is August while the driest month is November.

7-Day Weather Forecast in Winter Park

Tue, 29 Nov
80°
62°

0%

10 h

7 mi/h

Wed, 30 Nov
84°
66°

5%

8 h

5 mi/h

Thu, 1 Dec
71°
66°

10%

1 h

11 mi/h

Fri, 2 Dec
75°
68°

10%

2 h

9 mi/h

Sat, 3 Dec
80°
64°

0%

10 h

5 mi/h

Sun, 4 Dec
80°
64°

0%

10 h

6 mi/h

Mon, 5 Dec
80°
66°

0%

4 h

5 mi/h

Accommodations for your vacation in Winter Park

47 out of the 160 listed accommodations in Winter Park are house rental. They account for many of the accommodation types in this destination (62.67%). In addition, house rental there have an average cost of $330 per night as well as an average size of 1,540 ft². Moreover, these accommodations are a great choice for large groups, as most can welcome 8 people. Apartment rental are the second most typical accommodation option in Winter Park. The average size of apartment rental in Winter Park is 1,030 ft², and the average price is $202 per night.
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 House rental and Apartment rental in Winter Park is $65 per night.

How many vacation rentals are available to book in Winter Park?

November has the highest amount of available House rental and Apartment rental in Winter Park, so you can expect plenty of offers, even for last-minute bookings.

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, TV, and Yard.

How many vacation rentals are in Winter Park?

Discover 160 vacation rentals available to book in Winter Park.

Are pets allowed in vacation rentals in Winter Park?

Yes, there are 46 vacation homes in Winter Park that allow pets, with an average price of $350 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 54 °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 VacationRentals.com Vacation Rentals in Winter Park HouseTrip Vacation Rentals in Winter Park FlipKey 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 Novasol Vacation Rentals in Winter Park HomeEscape Vacation Rentals in Winter Park

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