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Winter Garden Vacation Rentals

Find 225 available offers from 6 partners
Winter Garden
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed and breakfast
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+

Vacation rentals and apartments with air conditioning

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

House  Winter Garden
May 25 - Jun 1
$186 per night
House ∙ 7 guests ∙ 3 bedrooms

House in Winter Garden with Grill, Yard & Patio

4.8
Outstanding (28 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
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House  Winter Garden
Mar 23 - Mar 30
$63 per night
House ∙ 2 guests ∙ 1 bedroom

Nice House in Winter Garden

4.7
Excellent (3 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
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House  Winter Garden
Mar 30 - Apr 6
-23%
$181
$140 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Winter Garden with Free Parking

5.0
Outstanding (1 rating)
Winter Garden, 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 Garden rental with full kitchen.

Cottage  Winter Garden
Nov 9 - Nov 16
$172 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Winter Garden with Grill

Winter Garden, Orange County, Florida, United States
Kitchen
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Apartment  Winter Garden
Mar 23 - Mar 30
$126 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment in Winter Garden

5.0
Outstanding (3 ratings)
Winter Garden, Orange County, Florida, United States
Kitchen
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House  Winter Garden
Feb 9 - Feb 16
$171 per night
House ∙ 8 guests ∙ 3 bedrooms

Family Friendly Vacation Home in Winter Garden with Free Parking

4.9
Outstanding (8 ratings)
Winter Garden, Orange County, Florida, United States
Kitchen
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Vacation rentals with Wi-Fi

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

House  Winter Garden
May 11 - May 18
-30%
$612
$427 per night
House ∙ 8 guests ∙ 4 bedrooms

Nice House in Winter Garden with Yard, Grill & Patio + Sunrise Views

4.9
Outstanding (25 ratings)
Winter Garden, Orange County, Florida, United States
Internet
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House  Winter Garden
Feb 8 - Feb 15
$309 per night
House ∙ 8 guests ∙ 2 bedrooms

Wonderful House in Winter Garden with Pool

Winter Garden, Orange County, Florida, United States
Internet
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House  Winter Garden
Apr 20 - Apr 27
$150 per night
House ∙ 4 guests ∙ 2 bedrooms

Charming Vacation Home in Winter Garden with Patio & Yard

4.8
Outstanding (31 ratings)
Winter Garden, Orange County, Florida, United States
Internet
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Best Vacation Home Deals in Winter Garden

Save up to 47%

Cottage Winter Garden
Mar 31 - Apr 7
-21%
$303
$240 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Winter Garden

Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Apr 20 - Apr 27
-47%
$199
$106 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Winter Garden with Patio

5.0
Outstanding (9 ratings)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Apr 13 - Apr 20
-28%
$155
$112 per night
House ∙ 4 guests ∙ 1 bedroom

House in Winter Garden with Grill, Patio & Yard

5.0
Outstanding (52 ratings)
Winter Garden, Orange County, Florida, United States
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Recommended Vacation Rentals in Winter Garden

Find your perfect vacation rental in Winter Garden: from $63 per night

House Winter Garden
Apr 20 - Apr 27
-40%
$209
$125 per night
House ∙ 4 guests ∙ 2 bedrooms

Lovely Vacation Home in Winter Garden with Decorative Fireplace

5.0
Outstanding (45 ratings)
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Apr 19 - Apr 26
-65%
$403
$141 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Rental Cottage in Winter Garden with Yard & Patio

4.9
Outstanding (52 ratings)
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Apr 20 - Apr 27
-54%
$210
$98 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Winter Garden

5.0
Outstanding (9 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
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House Winter Garden
Apr 13 - Apr 20
-38%
$167
$103 per night
House ∙ 4 guests ∙ 1 bedroom

House in Winter Garden with Grill & Yard

5.0
Outstanding (52 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
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Apartment Winter Garden
May 25 - Jun 1
$109 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Winter Garden

5.0
Outstanding (1 rating)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Oct 25 - Nov 1
-24%
$254
$192 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Winter Garden

Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Jun 15 - Jun 22
$188 per night
Cottage ∙ 7 guests ∙ 3 bedrooms

Cottage in Winter Garden

Winter Garden, Orange County, Florida, United States
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House Winter Garden
Apr 20 - Apr 27
$176 per night
House ∙ 6 guests ∙ 3 bedrooms

Charming Vacation Home in Winter Garden with Yard & Patio

5.0
Outstanding (12 ratings)
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Mar 9 - Mar 16
$212 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Winter Garden

Winter Garden, Orange County, Florida, United States
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Budget-friendly Vacation Rentals in Winter Garden

Find Fantastic yet Inexpensive Offers

Cottage Winter Garden
Apr 16 - Apr 23
-63%
$401
$149 per night
Cottage ∙ 8 guests ∙ 1 bedroom

Cottage in Winter Garden with Patio & Grill

Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Jul 13 - Jul 20
$141 per night
Cottage ∙ 7 guests ∙ 3 bedrooms

Nice Cottage in Winter Garden

5.0
Outstanding (3 ratings)
Winter Garden, Orange County, Florida, United States
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Apartment Winter Garden
Apr 6 - Apr 13
$135 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Pleasant Apartment in Winter Garden

5.0
Outstanding (1 rating)
Winter Garden, Orange County, Florida, United States
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Top-Rated Rentals and Accommodations in Winter Garden

Book Vacation Rental Offers with the Highest User Rating

Apartment Winter Garden
May 25 - Jun 1
$114 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Lovely Apartment in Winter Garden

4.7
Excellent (3 ratings)
Winter Garden, Orange County, Florida, United States
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Apartment Winter Garden
May 25 - Jun 1
$109 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Winter Garden

5.0
Outstanding (2 ratings)
Winter Garden, Orange County, Florida, United States
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Apartment Winter Garden
Mar 16 - Mar 23
$80 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment in Winter Garden

5.0
Outstanding (1 rating)
Winter Garden, Orange County, Florida, United States
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Popular Rental Amenities in Winter Garden

  • Pet-friendly (47)
  • Pool (130)
  • Air conditioning (224)
  • WiFi (228)
  • Kitchen (159)
  • Washing machine (103)
  • TV (201)
  • Parking (13)
  • Microwave (185)
  • Balcony/patio (42)
  • Dishwasher (122)
  • Yard (35)

Many users pay a closer look at the vacation rentals including a pool. More than half of the properties have one in this destination. Hotel room with pools in Winter Garden are a wonderful choice for groups of 9 and usually cost around $198 a night. If you would also like to be close to the water, more than half of the accommodations providing a pool are located within 2 miles of the waterfront.

7-Day Weather Forecast in Winter Garden

Wed, 21 Feb
64°
60°

0%

6 h

9 mi/h

Thu, 22 Feb
69°
66°

0%

6 h

1 mi/h

Fri, 23 Feb
69°
66°

15%

0 h

16 mi/h

Sat, 24 Feb
66°
60°

10%

4 h

13 mi/h

Sun, 25 Feb
69°
69°

10%

6 h

4 mi/h

Mon, 26 Feb
75°
73°

10%

6 h

6 mi/h

Tue, 27 Feb
77°
75°

0%

5 h

11 mi/h

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 225 rentals
💳 Possible discounts up to 31%
🌙 Nightly prices starting at $63
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 47 homes
🏊 Vacation rentals with pools 131 homes

Frequently Asked Questions

What is the average nightly price for a vacation rental in Winter Garden?

The nightly price of accommodations in Winter Garden starts at $63. If you would like to stay in a house rental, the average price is $288 per night. A cabin Winter Garden will cost $271 per night on average.

How many vacation rentals are available for booking in Winter Garden?

Currently there are 225 vacation rentals in Winter Garden to browse and rent for your next trip.

What are the most popular amenities for vacation homes in Winter Garden?

Most travelers look for Pets allowed, Pool, and Air conditioning when booking a vacation rental in Winter Garden.

How many vacation homes with pools are there in Winter Garden?

There are 131 vacation rentals across 6 providers in Winter Garden.

Are pets allowed in vacation homes in Winter Garden?

Finding a vacation rental in Winter Garden that allows pets is possible, with 47 pet-friendly available.

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