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Winter Garden Vacation Rentals

Find 191 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+
3.5+

Best Vacation Home Deals in Winter Garden

Save up to 72%

House Winter Garden
Nov 11 - Nov 18
-72%
$347
$97 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Winter Garden with Free Parking
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Oct 21 - Oct 28
-41%
$593
$347 per night
House ∙ 8 guests ∙ 4 bedrooms
Nice House in Winter Garden with Yard & Grill + Sunrise Views
4.9
Outstanding (17 ratings)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Oct 10 - Oct 17
-59%
$290
$119 per night
House ∙ 4 guests ∙ 2 bedrooms
Lovely Vacation Home in Winter Garden with Decorative Fireplace
5.0
Outstanding (30 ratings)
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

Villa Winter Garden
Sep 27 - Oct 4
$100 per night
Villa ∙ 8 guests ∙ 3 bedrooms
Family Friendly Duplex Villa in Winter Garden with Grill & Yard
4.7
Excellent (26 ratings)
Winter Garden, Orange County, Florida, United States
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Apartment Winter Garden
Oct 22 - Oct 29
$81 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Rental Apartment in Winter Garden with Pool
5.0
Outstanding (1 rating)
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Mar 23 - Mar 30
$141 per night
Cottage ∙ 7 guests ∙ 3 bedrooms
Nice Cottage in Winter Garden
5.0
Outstanding (1 rating)
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 $56 per night

Apartment Winter Garden
Mar 23 - Mar 30
$84 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Winter Garden
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Jan 20 - Jan 27
$186 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Winter Garden with Grill & Yard
4.7
Excellent (26 ratings)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Jun 22 - Jun 29
$184 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming Vacation Home in Winter Garden with Yard
5.0
Outstanding (8 ratings)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Sep 26 - Oct 3
$91 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Winter Garden with Pool, Yard & Grill + Panoramic Views
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Jun 22 - Jun 29
$167 per night
House ∙ 8 guests ∙ 3 bedrooms
Family Friendly Vacation Home in Winter Garden with Free Parking
5.0
Outstanding (4 ratings)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Oct 8 - Oct 15
-56%
$223
$98 per night
House ∙ 4 guests ∙ 1 bedroom
House in Winter Garden with Grill & Yard
4.9
Outstanding (41 ratings)
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Sep 30 - Oct 7
-50%
$205
$103 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Winter Garden with Pool & Yard
5.0
Outstanding (8 ratings)
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Oct 10 - Oct 17
-53%
$278
$130 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Rental Cottage in Winter Garden with Yard
4.9
Outstanding (42 ratings)
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Dec 2 - Dec 9
$132 per night
Cottage ∙ 7 guests ∙ 3 bedrooms
Cottage in Winter Garden
Winter Garden, Orange County, Florida, United States
Free cancellation
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Budget-friendly Vacation Rentals in Winter Garden

Find Fantastic yet Inexpensive Offers

Cottage Winter Garden
Oct 8 - Oct 15
-56%
$271
$119 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Winter Garden with Grill
Winter Garden, Orange County, Florida, United States
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Cottage Winter Garden
Mar 23 - Mar 30
$171 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
Oct 14 - Oct 21
-68%
$326
$106 per night
House ∙ 4 guests ∙ 1 bedroom
Vacation Home in Winter Garden with Outdoor Pool
Winter Garden, Orange County, Florida, United States
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Vacation rentals and apartments with air conditioning

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

Cottage Winter Garden
Sep 30 - Oct 7
-50%
$251
$125 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Winter Garden
Winter Garden, Orange County, Florida, United States
Air conditioning
Details
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House Winter Garden
Nov 11 - Nov 18
-68%
$978
$318 per night
House ∙ 12 guests ∙ 3 bedrooms
Vacation Home in Winter Garden with Private Parking
Winter Garden, Orange County, Florida, United States
Air conditioning
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Apartment Winter Garden
Dec 23 - Dec 30
$98 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Apartment in Winter Garden
Winter Garden, Orange County, Florida, United States
Air conditioning
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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
Nov 11 - Nov 18
-64%
$326
$117 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Winter Garden with Pool & Grill
Winter Garden, Orange County, Florida, United States
Internet
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Cottage Winter Garden
Dec 23 - Dec 30
$251 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Winter Garden
Winter Garden, Orange County, Florida, United States
Internet
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House Winter Garden
Oct 28 - Nov 4
-59%
$268
$110 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Winter Garden with Decorative Fireplace
Winter Garden, Orange County, Florida, United States
Free cancellation
Internet
Details
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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
Feb 10 - Feb 17
-25%
$261
$196 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Winter Garden with Grill
Winter Garden, Orange County, Florida, United States
Kitchen
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Cottage Winter Garden
Sep 30 - Oct 7
-52%
$200
$95 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Winter Garden
Winter Garden, Orange County, Florida, United States
Kitchen
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House Winter Garden
Nov 11 - Nov 18
-67%
$652
$212 per night
House ∙ 8 guests ∙ 2 bedrooms
Vacation Home in Winter Garden with Private Parking
Winter Garden, Orange County, Florida, United States
Kitchen
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Popular Rental Amenities in Winter Garden

  • Pet-friendly (24)
  • Pool (122)
  • Air conditioning (189)
  • WiFi (196)
  • Kitchen (135)
  • Washing machine (88)
  • TV (175)
  • Parking (14)
  • Microwave (167)
  • Balcony/patio (34)
  • Dishwasher (99)
  • Yard (40)

Many users pay a closer look at the vacation rentals including a pool. Many of the properties have one in this destination. Hotel room with pools in Winter Garden are a wonderful choice for groups of 7 and usually cost around $220 a night. If you would also like to be close to the water, many of the accommodations providing a pool are located within 2 miles of the waterfront.

7-Day Weather Forecast in Winter Garden

Mon, 25 Sep
89°
73°

10%

10 h

8 mi/h

Tue, 26 Sep
89°
73°

0%

8 h

10 mi/h

Wed, 27 Sep
87°
73°

15%

4 h

8 mi/h

Thu, 28 Sep
86°
73°

15%

4 h

10 mi/h

Fri, 29 Sep
84°
75°

15%

1 h

13 mi/h

Sat, 30 Sep
84°
75°

15%

2 h

14 mi/h

Sun, 1 Oct
86°
75°

15%

3 h

16 mi/h

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 191 homes
💳 Possible discounts up to 45%
🌙 Nightly prices starting at $56
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 21 homes
🏊 Vacation rentals with pools 121 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 $56. If you would like to stay in a house rental, the average price is $331 per night. A cabin Winter Garden will cost $262 per night on average.

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

Currently there are 191 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 121 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 21 pet-friendly available.

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