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Winter Park Vacation Rentals

Find 147 available offers from 6 partners
Winter Park
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
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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Best Vacation Home Deals in Winter Park

Save up to 28%

House Winter Park
Jun 22 - Jun 29
-28%
$250
$180 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Winter Park with Yard
4.5
Excellent (4 ratings)
Winter Park, Orange County, Florida, United States
Details
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Cottage Winter Park
Nov 11 - Nov 18
-20%
$244
$196 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Historic Cottage in Winter Park with Grill & Yard
5.0
Outstanding (59 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
Sep 14 - Sep 21
-28%
$241
$174 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Winter Park with Grill
Winter Park, Orange County, Florida, United States
Details
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Discover a vacation rental that meets your criteria among the 147 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 6 different providers.

Top-Rated Rentals and Accommodations in Winter Park

Book Vacation Rental Offers with the Highest User Rating

House Winter Park
Jun 22 - Jun 29
$200 per night
House ∙ 12 guests ∙ 4 bedrooms
Charming Vacation Home in Winter Park
5.0
Outstanding (9 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
Jan 6 - Jan 13
$65 per night
House ∙ 2 guests ∙ 1 bedroom
Beautiful House in Winter Park
4.5
Excellent (6 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
Mar 9 - Mar 16
$150 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Winter Park
5.0
Outstanding (1 rating)
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 $60 per night

House Winter Park
Jan 13 - Jan 20
$237 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful House in Winter Park with Grill & Yard
4.2
Very good (9 ratings)
Winter Park, Orange County, Florida, United States
Details
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Condo Winter Park
Jan 19 - Jan 26
$375 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Winter Park with Private Patio
Winter Park, Orange County, Florida, United States
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House Winter Park
Jan 19 - Jan 26
$299 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Winter Park
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Mar 2 - Mar 9
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Winter Park with Yard
5.0
Outstanding (50 ratings)
Winter Park, Orange County, Florida, United States
Details
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House Winter Park
Jun 8 - Jun 15
$300 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Winter Park with Grill, Pool & Yard
4.9
Outstanding (132 ratings)
Winter Park, Orange County, Florida, United States
Details
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Apartment Winter Park
Jan 20 - Jan 27
$120 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Winter Park with Private Garden
5.0
Outstanding (3 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Jan 13 - Jan 20
$132 per night
House ∙ 3 guests ∙ 1 bedroom
Lovely Vacation Home in Winter Park
5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
Details
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Apartment Winter Park
Jan 19 - Jan 26
$176 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
Private Rental Apartment in Winter Park
4.7
Excellent (6 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Oct 9 - Oct 16
$110 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Winter Park
5.0
Outstanding (1 rating)
Winter Park, Orange County, Florida, United States
Details
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Budget-friendly Vacation Rentals in Winter Park

Find Fantastic yet Inexpensive Offers

House Winter Park
Jun 22 - Jun 29
$120 per night
House ∙ 4 guests ∙ 3 bedrooms
House in Winter Park
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Jan 5 - Jan 12
-18%
$123
$101 per night
Apartment ∙ 6 guests ∙ 1 bedroom
Rental Apartment in Winter Park
5.0
Outstanding (6 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Jan 13 - Jan 20
$122 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Winter Park
4.9
Outstanding (52 ratings)
Winter Park, Orange County, Florida, United States
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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  Winter Park
Oct 1 - Oct 8
-18%
$122
$100 per night
Apartment ∙ 6 guests ∙ 1 bedroom
Rental Apartment in Winter Park
Winter Park, Orange County, Florida, United States
Air conditioning
Details
Vacasa
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House  Winter Park
Jan 20 - Jan 27
$114 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Winter Park
Winter Park, Orange County, Florida, United States
Air conditioning
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House  Winter Park
Jan 6 - Jan 13
$176 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Winter Park
5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Air conditioning
Details
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Vacation rentals with Wi-Fi

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

House  Winter Park
Jan 27 - Feb 3
$60 per night
House ∙ 2 guests ∙ 1 bedroom
Whole Vacation Home in Goldenrod
4.9
Outstanding (33 ratings)
Winter Park, Orange County, Florida, United States
Internet
Details
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House  Winter Park
Dec 5 - Dec 12
$83 per night
House ∙ 3 guests ∙ 1 bedroom
Nice House in Orlando with Pool & Yard
4.9
Outstanding (137 ratings)
Winter Park, Orange County, Florida, United States
Internet
Details
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House  Winter Park
Apr 6 - Apr 13
-48%
$244
$128 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Rosemont with Yard & Grill
4.6
Excellent (13 ratings)
Winter Park, Orange County, Florida, United States
Internet
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Winter Park with their own private patios and balconies.

House  Winter Park
Nov 2 - Nov 9
$129 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Forest City with Yard & Grill
Winter Park, Orange County, Florida, United States
Balcony
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House  Winter Park
Jun 22 - Jun 29
$277 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Northeast Orlando
Winter Park, Orange County, Florida, United States
Balcony
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House  Winter Park
Jan 13 - Jan 20
$266 per night
House ∙ 2 guests ∙ 1 bedroom
House in Colonialtown South with Yard & Grill
Winter Park, Orange County, Florida, United States
Balcony
Details
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Popular Rental Amenities in Winter Park

  • Pool (47)
  • Pet-friendly (44)
  • WiFi (147)
  • Air conditioning (132)
  • Kitchen (89)
  • TV (131)
  • Parking (9)
  • Washing machine (71)
  • Microwave (68)
  • Dishwasher (40)
  • Balcony/patio (36)
  • No smoking (115)

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're dreaming of days spent poolside or you are looking for a pet-friendly rental, as the most frequently offered features are "Pool" and "Pets allowed." Not as many rentals in Winter Park are available if you need a wheelchair accessible vacation rental or if you need a fenced-in backyard as "Fenced" and "Wheelchair accessible" are not very popular amenities in Winter Park.

The Weather in Winter Park

max.
Min.
72°
54°
9 days 9
max.
Min.
75°
55°
7 days 7
max.
Min.
79°
59°
7 days 7
max.
Min.
84°
66°
8 days 8
max.
Min.
88°
70°
9 days 9
max.
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90°
73°
17 days 17
max.
Min.
91°
75°
17 days 17
max.
Min.
91°
75°
19 days 19
max.
Min.
90°
75°
16 days 16
max.
Min.
84°
68°
7 days 7
max.
Min.
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 54° low. The rainiest month is August while the driest month is November.

7-Day Weather Forecast in Winter Park

Wed, 27 Sep
93°
75°

10%

6 h

8 mi/h

Thu, 28 Sep
93°
77°

10%

4 h

7 mi/h

Fri, 29 Sep
87°
77°

10%

7 h

9 mi/h

Sat, 30 Sep
91°
77°

15%

4 h

9 mi/h

Sun, 1 Oct
91°
78°

15%

6 h

12 mi/h

Mon, 2 Oct
86°
77°

15%

3 h

16 mi/h

Tue, 3 Oct
87°
69°

0%

10 h

7 mi/h

Accommodations for your vacation in Winter Park

50 out of the 147 listed accommodations in Winter Park are house rental. They account for many of the accommodation types in this destination (62.5%). In addition, house rental there have an average cost of $255 per night as well as an average size of 114 m². Moreover, these accommodations are a great choice for medium-sized groups and families, as most can welcome 5 people. Apartment rental are the second most typical accommodation option in Winter Park. The average size of apartment rental in Winter Park is 118 m², and the average price is $203 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.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 147 homes
💳 Possible discounts up to 32%
🌙 Nightly prices starting at $60
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 42 homes
🏊 Vacation rentals with pools 47 homes

Frequently Asked Questions

What is the typical nightly price for a vacation home in Winter Park?

The nightly price of accommodations in Winter Park starts at $60. If you would like to stay in a house rental, the average price is $255 per night. A apartment rental Winter Park will cost $203 per night on average.

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

There are 147 vacation rentals from 6 providers in Winter Park.

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

If you're looking to book a vacation rental in Winter Park, the most popular amenities are: Pets allowed, Pool and Internet.

How many vacation rentals with a pool are in Winter Park?

There are 47 vacation rentals from 6 providers in Winter Park.

Are dogs allowed in vacation rentals in Winter Park?

In case if you are traveling with a pet in Winter Park - 29% of rentals are pet-friendly.

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

Winter Park has its warmest time of year in July and August, with average nightly prices being around $60.

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