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Winter Garden Vacation Rentals

Find 222 available offers from 7 partners
Winter Garden
Anytime
Guests
Winter Garden
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Winter Garden

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

Vacation rentals and apartments with air conditioning

House  Winter Garden
Jul 6 - Jul 13
-55%
$268
$120 per night
House ∙ 4 guests ∙ 2 bedrooms

Lovely Vacation Home in Winter Garden with Decorative Fireplace

4.9
Outstanding (93 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
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House  Winter Garden
Jul 6 - Jul 13
-55%
$218
$98 per night
House ∙ 4 guests ∙ 1 bedroom

House in Winter Garden with Grill, Patio & Yard

5.0
Outstanding (103 ratings)
Winter Garden, Orange County, Florida, United States
Air conditioning
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Cottage  Winter Garden
Aug 17 - Aug 24
$120 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Rental Cottage in Winter Garden with Yard & Patio

4.8
Outstanding (106 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
Air conditioning
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Vacation homes and rentals with a yard

House  Winter Garden
Sep 2 - Sep 9
-70%
$266
$81 per night
House ∙ 5 guests ∙ 2 bedrooms

House in Oakland with Yard

Winter Garden, Orange County, Florida, United States
Free cancellation
Yard
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House  Winter Garden
Jul 6 - Jul 13
$150 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Horizon West with Grill & Yard

4.8
Outstanding (23 ratings)
Winter Garden, Orange County, Florida, United States
Yard
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House  Winter Garden
Sep 21 - Sep 28
$215 per night
House ∙ 6 guests ∙ 3 bedrooms

Entire Vacation Home in Minneola with Beautiful Pool + Pond View

5.0
Outstanding (26 ratings)
Winter Garden, Orange County, Florida, United States
Yard
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Best vacation rentals with a balcony

Cottage  Winter Garden
Aug 3 - Aug 10
$121 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Wonderful Cottage in Montverde with Grill & Patio + Lake View

5.0
Outstanding (218 ratings)
Winter Garden, Orange County, Florida, United States
Balcony
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Condo  Winter Garden
Jul 23 - Jul 30
$91 per night
Condo ∙ 3 guests ∙ 1 bedroom

Luxurious Condo in Orlando with Pool, Patio & Yard + Amazing Views + Close to Beach

4.3
Very good (8 ratings)
Winter Garden, Orange County, Florida, United States
Balcony
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Condo  Winter Garden
Jul 23 - Jul 30
$138 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo in Florida Center with Pool + Amazing Views

Winter Garden, Orange County, Florida, United States
Balcony
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Best Vacation Home Deals in Winter Garden

Save up to 59%

House Winter Garden
Jul 6 - Jul 13
-59%
$268
$110 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Winter Garden with Decorative Fireplace

4.9
Outstanding (93 ratings)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Jun 29 - Jul 6
-59%
$218
$90 per night
House ∙ 4 guests ∙ 1 bedroom

House in Winter Garden with Grill, Yard & Patio

5.0
Outstanding (103 ratings)
Winter Garden, Orange County, Florida, United States
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Bed and breakfast Winter Garden
Jul 20 - Jul 27
-27%
$198
$145 per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom

Lovely Bed & Breakfast in Winter Garden with Patio & Yard

4.6
Excellent
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 $53 per night

Studio flat Winter Garden
Jul 13 - Jul 20
-70%
$256
$76 per night
Studio flat ∙ 4 guests ∙ 1 bedroom

Studio in Orlando with Hot Tub & Pool

Winter Garden, Orange County, Florida, United States
Free cancellation
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Condo Winter Garden
Jul 24 - Jul 31
-55%
$175
$79 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Orlando with Pool, Hot Tub + Lake Views

4.0
Very good
Winter Garden, Orange County, Florida, United States
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Apartment Winter Garden
Aug 10 - Aug 17
-44%
$107
$60 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment in Orlando with Hot Tub, Grill & Yard

Winter Garden, Orange County, Florida, United States
Free cancellation
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Studio flat Winter Garden
Aug 10 - Aug 17
-44%
$92
$52 per night
Studio flat ∙ 4 guests ∙ 1 bedroom

Studio in Orlando with Yard, Pool & Jacuzzi

Winter Garden, Orange County, Florida, United States
Free cancellation
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Resort Winter Garden
Sep 3 - Sep 10
-37%
$165
$103 per night
Resort ∙ 127 guests ∙ 2 bedrooms

Nice Resort in Orlando with Outdoor Pool

3.9
Good (1 rating)
Winter Garden, Orange County, Florida, United States
Free cancellation
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House Winter Garden
Aug 3 - Aug 10
-39%
$305
$187 per night
House ∙ 10 guests ∙ 3 bedrooms

House in Apopka with Optional Pool

4.8
Outstanding (72 ratings)
Winter Garden, Orange County, Florida, United States
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Resort Winter Garden
Jun 30 - Jul 7
-83%
$794
$138 per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort in Florida Center with Outdoor Pool

4.6
Excellent
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Aug 11 - Aug 18
-53%
$348
$162 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Signal Hill with Yard & Grill

4.8
Outstanding (42 ratings)
Winter Garden, Orange County, Florida, United States
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Apartment Winter Garden
Aug 24 - Aug 31
$94 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Orlando with Patio, Grill & Pool

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

Find Fantastic yet Inexpensive Offers

House Winter Garden
Sep 7 - Sep 14
-22%
$167
$130 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Orlando with Jacuzzi & Pool

Winter Garden, Orange County, Florida, United States
Free cancellation
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House Winter Garden
Sep 7 - Sep 14
$216 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Clermont with Patio, Yard & Pool

5.0
Outstanding (5 ratings)
Winter Garden, Orange County, Florida, United States
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House Winter Garden
Aug 10 - Aug 17
-53%
$321
$149 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Rosemont with Grill & Yard

4.6
Excellent (7 ratings)
Winter Garden, Orange County, Florida, United States
Free cancellation
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Top-Rated Rentals and Accommodations in Winter Garden

Book Vacation Rental Offers with the Highest User Rating

House Winter Garden
Sep 7 - Sep 14
$378 per night
House ∙ 12 guests ∙ 4 bedrooms

Lovely Vacation Home in Metro West with Outside Pool

4.5
Excellent (185 ratings)
Winter Garden, Orange County, Florida, United States
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Mobile home Winter Garden
Sep 7 - Sep 14
$60 per night
Mobile home ∙ 6 guests ∙ 3 bedrooms

Mobile Home in Orlando with Patio, Pool & Grill

5.0
Outstanding (5 ratings)
Winter Garden, Orange County, Florida, United States
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Mobile home Winter Garden
Jul 6 - Jul 13
$90 per night
Mobile home ∙ 5 guests ∙ 2 bedrooms

Mobile Home in Apopka with Patio & Pool

4.5
Excellent (4 ratings)
Winter Garden, Orange County, Florida, United States
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Popular Rental Amenities in Winter Garden

  • Pet-friendly (43)
  • Pool (134)
  • Air conditioning (215)
  • WiFi (221)
  • Kitchen (154)
  • Washing machine (111)
  • TV (198)
  • Parking (12)
  • Microwave (174)
  • Balcony/patio (64)
  • Dishwasher (135)
  • Yard (64)

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 8 and usually cost around $179 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.

Information about vacation rentals in Winter Garden

🏡 Vacation rentals available 222 rentals
💳 Possible discounts up to 59%
🌙 Nightly prices starting at $53
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 43 homes
🏊 Vacation rentals with pools 134 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 $53. If you would like to stay in a house rental, the average price is $275 per night. A bed and breakfast rental Winter Garden will cost $202 per night on average.

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

Currently there are 222 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 134 vacation rentals across 7 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 43 pet-friendly available.

Find the perfect Winter Garden home to match your style

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