Winter Park Vacation Rentals - HomeToGo base64Hash

Winter Park Vacation Rentals

Find 201 available offers from 5 partners

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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.

Save up to 57%

Best Vacation Home Deals in Winter Park

Oct 21 - Oct 28

-37%

~~$276~~

$174 per night

House ∙ 15 guests ∙ 6 bedrooms

Vacation Home in Central Business District with Private Pool

4.5

"Outstanding" (164 ratings)

Winter Park, Orange County, Florida, United States

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Sep 16 - Sep 23

-57%

~~$241~~

$103 per night

House ∙ 6 guests ∙ 3 bedrooms

Wonderful Vacation Home in Goldenrod with Yard

4.8

"Excellent" (74 ratings)

Winter Park, Orange County, Florida, United States

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Sep 9 - Sep 16

-32%

~~$201~~

$136 per night

House ∙ 8 guests ∙ 3 bedrooms

Lovely House in Longwood with Grill & Yard

5.0

"Excellent" (39 ratings)

Winter Park, Orange County, Florida, United States

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Discover a vacation rental that meets your criteria among the 201 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.

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in Winter Park

May 27 - Jun 3

$373 per night

House ∙ 8 guests ∙ 5 bedrooms

Nice Vacation Home in Maitland with Outdoor Pool

4.9

"Excellent" (154 ratings)

Winter Park, Orange County, Florida, United States

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May 13 - May 20

-22%

~~$215~~

$168 per night

House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Winter Park with Yard

5.0

"Excellent" (1 rating)

Winter Park, Orange County, Florida, United States

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Apr 15 - Apr 22

$132 per night

House ∙ 3 guests ∙ 1 bedroom

Lovely Vacation Home in Winter Park

5.0

"Excellent" (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 $63 per night

Sep 30 - Oct 7

$373 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Winter Park with Grill, Pool & Yard

4.9

"Excellent" (115 ratings)

Winter Park, Orange County, Florida, United States

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May 27 - Jun 3

$63 per night

House ∙ 2 guests ∙ 1 bedroom

Beautiful House in Winter Park

Winter Park, Orange County, Florida, United States

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Jul 1 - Jul 8

$150 per night

Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Winter Park with Yard

5.0

"Excellent" (14 ratings)

Winter Park, Orange County, Florida, United States

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Dec 9 - Dec 16

$237 per night

Cottage ∙ 4 guests ∙ 2 bedrooms

Historic Cottage in Winter Park with Grill & Yard

5.0

"Excellent" (45 ratings)

Winter Park, Orange County, Florida, United States

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Jun 3 - Jun 10

$233 per night

Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Winter Park

Winter Park, Orange County, Florida, United States

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Sep 30 - Oct 7

$100 per night

Apartment ∙ 6 guests ∙ 1 bedroom

Modern Rental Apartment in Winter Park with Yard

Winter Park, Orange County, Florida, United States

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Jun 10 - Jun 17

$150 per night

House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Winter Park

Winter Park, Orange County, Florida, United States

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Jul 15 - Jul 22

$212 per night

House ∙ 12 guests ∙ 4 bedrooms

Charming Vacation Home in Winter Park

Winter Park, Orange County, Florida, United States

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Jun 3 - Jun 10

$176 per night

Apartment ∙ 8 guests ∙ 2 bedrooms

Private Rental Apartment in Winter Park

5.0

"Excellent" (1 rating)

Winter Park, Orange County, Florida, United States

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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Winter Park

Jun 3 - Jun 10

$177 per night

House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Winter Park

Winter Park, Orange County, Florida, United States

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Apr 7 - Apr 14

-16%

~~$375~~

$315 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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May 20 - May 27

$119 per night

Condo ∙ 4 guests ∙ 1 bedroom

Condo in Winter Park with Pool

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.

Sep 30 - Oct 7

$373 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Winter Park with Grill, Pool & Yard

4.9

"Excellent" (116 ratings)

Winter Park, Orange County, Florida, United States

Internet

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Sep 30 - Oct 7

$64 per night

House ∙ 2 guests ∙ 1 bedroom

Beautiful House in Winter Park

Winter Park, Orange County, Florida, United States

Internet

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Jul 1 - Jul 8

$150 per night

Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Winter Park with Yard

5.0

"Excellent" (15 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.

Sep 30 - Oct 7

$100 per night

Apartment ∙ 6 guests ∙ 1 bedroom

Modern Rental Apartment in Winter Park with Yard

Winter Park, Orange County, Florida, United States

Air conditioning

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Jun 10 - Jun 17

$150 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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Jun 3 - Jun 10

$177 per night

Apartment ∙ 8 guests ∙ 2 bedrooms

Private Rental Apartment in Winter Park

4.5

"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.

Jun 10 - Jun 17

$120 per night

Condo ∙ 4 guests ∙ 2 bedrooms

Charming Condo in Winter Park

Winter Park, Orange County, Florida, United States

Kitchen

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Jul 15 - Jul 22

$212 per night

House ∙ 12 guests ∙ 4 bedrooms

Charming Vacation Home in Winter Park

Winter Park, Orange County, Florida, United States

Kitchen

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Apr 15 - Apr 22

$132 per night

House ∙ 3 guests ∙ 1 bedroom

Lovely Vacation Home in Winter Park

5.0

"Excellent" (1 rating)

Winter Park, Orange County, Florida, United States

Kitchen

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Popular Rental Amenities in Winter Park

Internet (186)
Air conditioning (172)
TV (172)
No smoking (160)
Kitchen (128)
No pets (109)
Microwave (106)
Yard (100)
Washer (91)
Dishwasher (70)
Pool (66)
Pets allowed (57)

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. Min. 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

Sat, 1 Apr

87°

68°

Sun, 2 Apr

86°

69°

Mon, 3 Apr

93°

69°

Tue, 4 Apr

96°

69°

Wed, 5 Apr

93°

69°

Thu, 6 Apr

91°

71°

Fri, 7 Apr

87°

69°

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Accommodations for your vacation in Winter Park

64 out of the 201 listed accommodations in Winter Park are house rental. They account for more than half of the accommodation types in this destination (53.33%). In addition, house rental there have an average cost of $285 per night as well as an average size of 137 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 118 m², and the average price is $221 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	201 properties
💳 Possible discounts	up to 21%
🌙 Nightly prices starting at	$63
⭐ Popular amenities	Internet, Air conditioning and TV
🐾 Pet friendly accommodations	57 properties
🏊 Vacation rentals with pools	69 properties

Frequently Asked Questions

What is the average price per night for a vacation home in Winter Park?

The average accommodation in Winter Park is priced at $63 per night. If you’re interested in a house rental, the average price is $285 per night. A apartment rental Winter Park will cost $221 per night on average.

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

Currently there are 201 vacation rentals in Winter Park to browse and rent for your trip.

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

Three most popular amenities for home rentals in Winter Park include accommodations with: Internet, Air conditioning, and TV.

Are dogs allowed in vacation homes in Winter Park?

Sure, there are 57 vacation rentals in Winter Park that allow pets , with an average nightly rate of $299.

What are the best months to travel to Winter Park ?

If booking a vacation rental in Winter Park, keep in mind that rainy season is usually in August or June, with November often being the driest.

We list offers from thousands of providers, including:

Winter Park Vacation Rentals

Choose the perfect vacation rental

Rent a condo, or vacation home in Winter Park, on Orlando's doorstep

Best Vacation Home Deals in Winter Park

Top-Rated Rentals and Accommodations in Winter Park

Recommended Vacation Rentals in Winter Park

Budget-friendly Vacation Rentals in Winter Park

Vacation rentals with Wi-Fi

Vacation rentals and apartments with air conditioning

Apartments and vacation rentals with a kitchen

Popular Rental Amenities in Winter Park

The Weather in Winter Park

7-Day Weather Forecast in Winter Park

Accommodations for your vacation in Winter Park

Fine dining and cheap local eateries

Winter Park: historic and interesting sites

Tons of fun for families, too

Information about vacation rentals in Winter Park

Frequently Asked Questions

What is the average price per night for a vacation home in Winter Park?

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

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

Are dogs allowed in vacation homes in Winter Park?

What are the best months to travel to Winter Park ?

Vacation Destinations Near Winter Park

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