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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Winter Garden holiday homes

2 bedrooms, WiFi, bed sheets

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
9.6 out of 10, Exceptional, (12 reviews)
"One of best VRBO’s we have stayed. Very well set up and very warm and comfortable. Felt like home. And the location is perfect. We will be back. "
United States
John T.
The price is HK$1,506
HK$4,286 total
includes taxes & fees
27 Jul - 28 Jul
Fire Pit & Yard: Updated Winter Garden Home!
Pool

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Winter Garden
10.0 out of 10, Exceptional, (34 reviews)
"Great location and a comfortable stay. "
United States
Tim S.
The price is HK$2,416
HK$4,262 total
includes taxes & fees
22 Aug - 23 Aug
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Interior

FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.2 out of 10, Wonderful, (10 reviews)
"We had a great time! The host was spectacular. Our accommodations were very clean and comfortable! "
United States
Emily R.
The price is HK$941
HK$1,725 total
includes taxes & fees
27 Jul - 28 Jul
FunTropicalTinyHomeGolfCartLake
Interior

Central Florida's Historic Gem & wedding venue- The Oakland Manor House

Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
10.0 out of 10, Exceptional, (1 review)
"We had a spectacular time at the Oakland Manor House. It's a gorgeous, historic home filled with both handsome antiques and comfortable sofas and beds. The kitchen is fully stocked and a joy to use to make meals if you're so inclined. The bathrooms were very clean and well appointed with bath products and hair dryers for use. They even had coffee beans and a grinder for use. Very nice gestures. It was spotless and located in a lovely, safe neighborhood. We had a celebration of our wedding with...
United States
Kristen R.
The price is HK$4,902
HK$9,888 total
includes taxes & fees
31 Jul - 1 Aug
Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Private kitchen

Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL

Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL
Killarney
The price is HK$1,864
HK$4,789 total
includes taxes & fees
31 Jul - 1 Aug
Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL
Exterior

Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is HK$573
HK$2,204 total
includes taxes & fees
27 Jul - 28 Jul
Winter Garden Family-friendly Condo w Resort Pool
TV, ping pong

Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
Winter Garden
The price is HK$635
HK$2,306 total
includes taxes & fees
4 Aug - 5 Aug
Upstay Large Family Condo w Pool, Sauna
Outdoor pool

Private Spacious Room in Home, with Pool-The Oasis Room

Private Spacious Room in Home, with Pool-The Oasis Room
Clermont
9.6 out of 10, Exceptional, (34 reviews)
"Good"
United States
Blow
The price is HK$353
HK$766 total
includes taxes & fees
27 Jul - 28 Jul
Private Spacious Room in Home, with Pool-The Oasis Room
Smart TV, video games, printers

Mid-century Modern Villa w/ Pool Near Universal

Mid-century Modern Villa w/ Pool Near Universal
Orlando
10.0 out of 10, Exceptional, (28 reviews)
"Great location close to Universal! We really enjoyed the neighborhood which was great for walking our dog."
United States
Mike B.
Mid-century Modern Villa w/ Pool Near Universal
Exterior

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

Charming 2-bedroom apartment in house with AC, WiFi included
Apopka
9.8 out of 10, Exceptional, (31 reviews)
"Mrs Linda was so nice and very attentive. Place was nice and quiet."
United States
Maribel
The price is HK$812
HK$1,202 total
includes taxes & fees
3 Aug - 4 Aug
Charming 2-bedroom apartment in house with AC, WiFi included
Outdoor pool, pool umbrellas, pool loungers

Splash Pool Townhome at Festival Resort

Splash Pool Townhome at Festival Resort
3.0 star property
Festival
Splash Pool Townhome at Festival Resort
Smart TV

Rose's Lakeview

Rose's Lakeview
Orlando
8.8 out of 10, Excellent, (20 reviews)
"Comfortable, clean stay - good location for our event. "
United States
Kari B.
The price is HK$1,129
HK$3,308 total
includes taxes & fees
27 Jul - 28 Jul
Rose's Lakeview
Microwave, oven, stovetop

Charming 4-bedroom Pool house with WiFi, king bed, AC in lovely Orlando

Charming 4-bedroom Pool house with WiFi, king bed, AC in lovely Orlando
Orlando
10.0 out of 10, Exceptional, (11 reviews)
"Just wanted a place to stay close to the airport that had a pool. House was clean and located close to many restaurants.Pool was great, would definitely stay again"
United States
Heather M.
The price is HK$2,761
HK$3,474 total
includes taxes & fees
5 Aug - 6 Aug
Charming 4-bedroom Pool house with WiFi, king bed, AC in lovely Orlando
Indoor pool

Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views

Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Orlando
9.2 out of 10, Wonderful, (73 reviews)
"Really needs updating. The Mildew was in need of bleach in the bathrooms. We had a good time, but the place was fixed up with nothing but a paint brush, some of the areas were falling hazards and should be address."
United States
susan B.
Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Dining

4-bedroom house in welcoming Tavares with Pool. Boat friendly.

4-bedroom house in welcoming Tavares with Pool. Boat friendly.
Tavares
9.2 out of 10, Wonderful, (33 reviews)
"Worked out perfectly for 4 couples. Great stay!"
United States
Ruth M.
The price is HK$1,843
HK$4,617 total
includes taxes & fees
27 Jul - 28 Jul
4-bedroom house in welcoming Tavares with Pool. Boat friendly.
Front of property

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
4.5 star property
Lindfields
Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
Pool

* Luxury Pool * Hot Tub * 86 Inch TV *

* Luxury Pool * Hot Tub * 86 Inch TV *
Apopka
9.8 out of 10, Exceptional, (31 reviews)
"Great home. The house was open, very comfortable, would stay again. "
United States
Nickolas T.
* Luxury Pool * Hot Tub * 86 Inch TV *
Water park

Six BR Home at ChampionsGate Resort

Six BR Home at ChampionsGate Resort
5.0 star property
Champions Gate
Six BR Home at ChampionsGate Resort
Outdoor pool

Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is HK$463
HK$525 total
includes taxes & fees
5 Aug - 6 Aug
Maple Leaf Inn & Suites
Dining

Private house with pool Kissimmee/Orlando

Private house with pool Kissimmee/Orlando
Buena Ventura Lakes
9.8 out of 10, Exceptional, (58 reviews)
"House was clean, and the beds were comfortable. Check in and out was easy. "
United States
Darla F.
The price is HK$1,412
HK$3,141 total
includes taxes & fees
27 Jul - 28 Jul
Private house with pool Kissimmee/Orlando
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"This is the 2nd time I have stayed here in the past 2 months and both times I have had zero issues. The rooms are immaculate, there is zero noise from other guests, and it is also convenient to and from the Disney parks. The only complaint I have is that the front desk people could be a little friendlier. Both times i have been there, no matter who i have run into at the desk, they always seem miserable."
Stacie 3-night trip
Posted less than an hour ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Vacation Homes information

Number of reviews
376
Accommodation
28996 Vacation Homes
Lowest Price
HK$525
Highest Price
HK$9,888

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