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Winter Park Vacation Rentals

Find 175 available offers from 16 partners
Winter Park
Anytime
Guests
Winter Park
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Winter Park

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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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Vacation rentals with Wi-Fi

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

House  Winter Park
May 11 - May 18
-69%
$215
$68 per night
House ∙ 2 guests ∙ 1 bedroom

Vacation Home in Winter Park with Yard & Grill

Winter Park, Orange County, Florida, United States
Internet
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Apartment  Winter Park
Jun 17 - Jun 24
$95 per night
Apartment ∙ 6 guests ∙ 1 bedroom

Rental Apartment in Winter Park

5.0
Outstanding
Winter Park, Orange County, Florida, United States
Internet
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House  Winter Park
Jul 8 - Jul 15
$200 per night
House ∙ 12 guests ∙ 4 bedrooms

Charming Vacation Home in Winter Park with Grill & Patio

4.9
Outstanding (18 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.

House  Winter Park
Aug 3 - Aug 10
-69%
$365
$113 per night
House ∙ 5 guests ∙ 3 bedrooms

House in Winter Park

Winter Park, Orange County, Florida, United States
Free cancellation
Air conditioning
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House  Winter Park
Jun 17 - Jun 24
$213 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Winter Park with Grill & Pool

5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Air conditioning
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House  Winter Park
Jun 17 - Jun 24
$331 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Winter Park with Private Pool

5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
Air conditioning
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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.

Apartment  Winter Park
May 17 - May 24
$177 per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Private Rental Apartment in Winter Park

4.5
Excellent (10 ratings)
Winter Park, Orange County, Florida, United States
Kitchen
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House  Winter Park
Feb 15 - Feb 22
$318 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Winter Park with Patio, Grill & Pool

4.9
Outstanding (136 ratings)
Winter Park, Orange County, Florida, United States
Kitchen
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Apartment  Winter Park
May 17 - May 24
$120 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Winter Park with Private Garden

5.0
Outstanding (4 ratings)
Winter Park, Orange County, Florida, United States
Kitchen
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Best Vacation Home Deals in Winter Park

Save up to 60%

House Winter Park
May 28 - Jun 4
-40%
$226
$135 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Rosemont with Yard & Grill

4.8
Outstanding (34 ratings)
Winter Park, Orange County, Florida, United States
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Cottage Winter Park
Apr 20 - Apr 27
-60%
$422
$169 per night
Cottage ∙ 7 guests ∙ 3 bedrooms

Cottage in Orlando with Pool

Winter Park, Orange County, Florida, United States
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House Winter Park
Apr 21 - Apr 28
-57%
$168
$72 per night
House ∙ 4 guests ∙ 1 bedroom

House in Fern Park with Private Pool

4.7
Excellent (88 ratings)
Winter Park, Orange County, Florida, United States
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Discover a vacation rental that meets your criteria among the 175 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 16 different providers.

Recommended Vacation Rentals in Winter Park

Find your perfect vacation rental in Winter Park: from $64 per night

House Winter Park
Aug 24 - Aug 31
$85 per night
House ∙ 3 guests ∙ 1 bedroom

Nice House in Orlando with Pool, Yard & Patio

4.9
Outstanding (160 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Apr 19 - Apr 26
$177 per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Entire Rental Apartment in Winter Park

5.0
Outstanding (10 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Apr 19 - Apr 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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House Winter Park
Jun 29 - Jul 6
$215 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Longwood with Pool, Patio & Yard

5.0
Outstanding (1 rating)
Winter Park, Orange County, Florida, United States
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House Winter Park
Apr 19 - Apr 26
$165 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Winter Park with Yard & Patio

4.8
Outstanding (18 ratings)
Winter Park, Orange County, Florida, United States
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Condo Winter Park
May 17 - May 24
$357 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Winter Park with Grill, Yard & Patio

4.9
Outstanding (39 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Apr 19 - Apr 26
$177 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Winter Park

5.0
Outstanding (2 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Jun 17 - Jun 24
$122 per night
Apartment ∙ 6 guests ∙ 1 bedroom

Rental Apartment in Winter Park with Patio

5.0
Outstanding (24 ratings)
Winter Park, Orange County, Florida, United States
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Apartment Winter Park
Dec 1 - Dec 8
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Winter Park with Patio & Yard

5.0
Outstanding (87 ratings)
Winter Park, Orange County, Florida, United States
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Budget-friendly Vacation Rentals in Winter Park

Find Fantastic yet Inexpensive Offers

House Winter Park
Jul 1 - Jul 8
$76 per night
House ∙ 4 guests ∙ 1 bedroom

Nice House in Forest City with Yard, Pool & Grill

4.7
Excellent (64 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Apr 12 - Apr 19
$248 per night
House ∙ 12 guests ∙ 4 bedrooms

Vacation Home in Engelwood Park with Grill, Patio & Pool

4.9
Outstanding (13 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
May 25 - Jun 1
$140 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Signal Hill with Yard & Grill

4.7
Excellent (6 ratings)
Winter Park, Orange County, Florida, United States
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Top-Rated Rentals and Accommodations in Winter Park

Book Vacation Rental Offers with the Highest User Rating

House Winter Park
Aug 21 - Aug 28
$80 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Engelwood Park

5.0
Outstanding (1 rating)
Winter Park, Orange County, Florida, United States
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Cottage Winter Park
Apr 19 - Apr 26
$104 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage in Longwood with Yard & Patio

4.7
Excellent (23 ratings)
Winter Park, Orange County, Florida, United States
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House Winter Park
Sep 7 - Sep 14
$73 per night
House ∙ 2 guests ∙ 1 bedroom

House in Wekiva Springs with Large Patio

5.0
Outstanding (184 ratings)
Winter Park, Orange County, Florida, United States
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Popular Rental Amenities in Winter Park

  • Pool (55)
  • Pet-friendly (57)
  • WiFi (171)
  • Air conditioning (168)
  • Kitchen (116)
  • TV (155)
  • Parking (5)
  • Washing machine (93)
  • Microwave (90)
  • Dishwasher (54)
  • Balcony/patio (77)
  • No smoking (167)

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'd like to have a fenced-in yard as "Fenced" and "Wheelchair accessible" are not very popular amenities in Winter Park.

The Weather in Winter Park

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54°
9 days 9
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7 days 7
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59°
7 days 7
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66°
8 days 8
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9 days 9
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75°
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84°
68°
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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

Sun, 14 Apr
80°
78°

0%

6 h

4 mi/h

Mon, 15 Apr
84°
80°

0%

6 h

6 mi/h

Tue, 16 Apr
87°
82°

10%

6 h

12 mi/h

Wed, 17 Apr
91°
86°

10%

5 h

5 mi/h

Thu, 18 Apr
91°
91°

0%

1 h

5 mi/h

Fri, 19 Apr
95°
95°

0%

5 h

6 mi/h

Sat, 20 Apr
93°
89°

5%

1 h

9 mi/h

Accommodations for your vacation in Winter Park

53 out of the 175 listed accommodations in Winter Park are house rental. They account for many of the accommodation types in this destination (63.1%). In addition, house rental there have an average cost of $248 per night as well as an average size of 140 m². Moreover, these accommodations are a great choice for medium-sized groups and families, as most can welcome 6 people. Apartment rental are the second most typical accommodation option in Winter Park. The average size of apartment rental in Winter Park is 101 m², and the average price is $176 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 175 rentals
💳 Possible discounts up to 70%
🌙 Nightly prices starting at $64
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 56 homes
🏊 Vacation rentals with pools 55 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 $64. If you would like to stay in a house rental, the average price is $248 per night. A apartment rental Winter Park will cost $176 per night on average.

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

There are 175 vacation rentals from 16 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 55 vacation rentals from 16 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 - 32% 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 $64.

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