Winter Garden Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Browse Select Winter Garden Vacation Homes

Kissimmee Spacious Suite with Pool & Fitness Center
1 bedroom, iron/ironing board, WiFi, bed sheets

Kissimmee Spacious Suite with Pool & Fitness Center

8.8 out of 10, Excellent, (13)
"The property was nice and room was very clean and spacious and would stay here again without hesitation."
The price is CA $98
CA $140 total
includes taxes & fees
Sep 6 - Sep 7
Kissimmee Spacious Suite with Pool & Fitness Center
Family Vacation Room with 2 DBL Beds Near Must-see Attractions
Iron/ironing board, free internet, bed sheets, wheelchair access

Family Vacation Room with 2 DBL Beds Near Must-see Attractions

10.0 out of 10, Exceptional, (3)
"All that goods I loved and recomended "
The price is CA $80
CA $119 total
includes taxes & fees
Sep 6 - Sep 7
Family Vacation Room with 2 DBL Beds Near Must-see Attractions
Hotel with AC & WiFi in Kissimmee
1 bedroom, WiFi, bed sheets

Hotel with AC & WiFi in Kissimmee

The price is CA $87
CA $127 total
includes taxes & fees
Sep 9 - Sep 10
Hotel with AC & WiFi in Kissimmee
King Bed, Pet-Friendly, 15 Min to Parks, Amenities
Property grounds

King Bed, Pet-Friendly, 15 Min to Parks, Amenities

The price is CA $96
CA $276 total
includes taxes & fees
Sep 2 - Sep 3
King Bed, Pet-Friendly, 15 Min to Parks, Amenities
Upstay - Large Condo Near Disney w Pool and Gym
Interior

Upstay - Large Condo Near Disney w Pool and Gym

The price is CA $86
CA $372 total
includes taxes & fees
Sep 1 - Sep 2
Upstay - Large Condo Near Disney w Pool and Gym
WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
Fridge, microwave, oven, stovetop

WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn

10.0 out of 10, Exceptional, (27)
"property was extremely clean, beautiful view and convenient to an active downtown area!"
The price is CA $417
CA $737 total
includes taxes & fees
Sep 3 - Sep 4
WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
Upstay Family-Friendly Condo w Pool Near Disney
Pool

Upstay Family-Friendly Condo w Pool Near Disney

The price is CA $89
CA $376 total
includes taxes & fees
Sep 9 - Sep 10
Upstay Family-Friendly Condo w Pool Near Disney
Royal Park Orlando Modern Room with 2 DBL Beds & Tennis Court
Iron/ironing board, WiFi, bed sheets, wheelchair access

Royal Park Orlando Modern Room with 2 DBL Beds & Tennis Court

10.0 out of 10, Exceptional, (1)
"Before i book the stay here i went to read the reviews about the property, some where good and some bad. So for the price you kind have to have an idea of how is going to be. But let me tell i was amazing how nice the room was, so perfectly clean, and they dont have carpet on the floor of the room wich for me it show they have to keep everything looking clean and good. I will definitely will be caming back to this place"
The price is CA $80
CA $119 total
includes taxes & fees
Sep 6 - Sep 7
Royal Park Orlando Modern Room with 2 DBL Beds & Tennis Court
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1891)
"Beautiful, perfect for a family getaway"
The price is CA $135
CA $168 total
includes taxes & fees
Aug 28 - Aug 29
The Berkley, Orlando
Willow Bend
Outdoor pool, sun loungers

Willow Bend

4.0 star property
10.0 out of 10, Exceptional, (1)
"this house abuts woods and a slow river that made the property peaceful "
The price is CA $188
CA $811 total
includes taxes & fees
Aug 28 - Aug 29
Willow Bend
Super Trend
House, 6 Bedrooms, Private Pool | Private kitchen

Super Trend

2.0 star property
8.0 out of 10, Very good, (1)
"Had some inconveniences getting in since the property didn’t respond on time"
The price is CA $152
CA $519 total
includes taxes & fees
Aug 28 - Aug 29
Super Trend
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Interior

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

8.8 out of 10, Excellent, (95)
"This home was right where we needed, clean, spacious and the pool was lovely. "
The price is CA $136
CA $654 total
includes taxes & fees
Aug 31 - Sep 1
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Charming 2-bedroom apartment in house with AC, WiFi included
Interior

Charming 2-bedroom apartment in house with AC, WiFi included

10.0 out of 10, Exceptional, (3)
"Very nice place. Very clean. Would stay again"
The price is CA $131
CA $190 total
includes taxes & fees
Aug 28 - Aug 29
Charming 2-bedroom apartment in house with AC, WiFi included
Aster Cove
Outdoor pool

Aster Cove

4.0 star property
The price is CA $208
CA $873 total
includes taxes & fees
Aug 28 - Aug 29
Aster Cove
Banana Leaf Villa-Vintage Vibes Premium Room
Dining

Banana Leaf Villa-Vintage Vibes Premium Room

2.0 star property
The price is CA $119
CA $159 total
includes taxes & fees
Sep 2 - Sep 3
Banana Leaf Villa-Vintage Vibes Premium Room
Banana Leaf Villa-Vintage Vibes Premium Room
Dining

Banana Leaf Villa-Vintage Vibes Premium Room

2.0 star property
8.0 out of 10, Very good, (4)
"This is the perfect getaway spot! Very accessible, quiet area. I will definitely be booking again."
The price is CA $119
CA $159 total
includes taxes & fees
Sep 2 - Sep 3
Banana Leaf Villa-Vintage Vibes Premium Room
Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood!
Smart TV, fireplace, table tennis, books

Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood!

10.0 out of 10, Exceptional, (21)
"This house had everything you could imagine! Very well stocked. The host was amazing!"
Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood!
Quiet Oasis in Lovely Neighborhood
Pool

Quiet Oasis in Lovely Neighborhood

9.8 out of 10, Exceptional, (148)
"Hosts were wondeful. Nice quiet neighborhood. Our favorite part was definitely the pool. "
The price is CA $112
CA $264 total
includes taxes & fees
Aug 28 - Aug 29
Quiet Oasis in Lovely Neighborhood
Amazing 3Bedrooms/Near to Disney/Themed rooms
Fridge, microwave, oven, stovetop

Amazing 3Bedrooms/Near to Disney/Themed rooms

The price is CA $159
CA $521 total
includes taxes & fees
Aug 31 - Sep 1
Amazing 3Bedrooms/Near to Disney/Themed rooms
Spacious Fun & Convenient
Computer monitors, printers

Spacious Fun & Convenient

4.0 star property
10.0 out of 10, Exceptional, (2)
"Nice and clean property "
The price is CA $182
CA $435 total
includes taxes & fees
Sep 9 - Sep 10
Spacious Fun & Convenient
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Garden Hotel Reviews

Walt Disney World Swan

Walt Disney World Swan

10/10 Excellent
"The resort was very nice and the spaces around the hotels were very nice! Very convenient to all of Disney! "
Sharon 2-night trip
Posted 22 hours ago
Walt Disney World Swan

Price trends for Vacation Homes in Winter Garden

Price trends for Vacation Homes in Winter Garden

Less expensive
More expensive
Next month
August
March
CA $138
Month
Price
January
CA $204
February
CA $218
March
CA $235
April
CA $208
May
CA $168
June
CA $228
July
CA $216
August
CA $131
September
CA $138
October
CA $164
November
CA $168
December
CA $220
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Vacation Homes in Winter Garden. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Winter Garden

Find out more about Winter Garden

Winter Garden Vacation Homes information

Number of reviews
3,088
Accommodation
30462 Vacation Homes
Lowest Price
CA $135
Highest Price
CA $372

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