Holiday Homes in Winter Garden

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Winter Garden

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

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

The price is NZ$410
includes taxes & fees
31 Aug - 1 Sept
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 NZ$504
includes taxes & fees
31 Aug - 1 Sept
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 NZ$938
includes taxes & fees
15 Sept - 16 Sept
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 NZ$487
includes taxes & fees
9 Sept - 10 Sept
Upstay Family-Friendly Condo w Pool Near Disney
Comfy room with private bathroom
1 bedroom, WiFi, bed sheets

Comfy room with private bathroom

The price is NZ$245
includes taxes & fees
30 Aug - 31 Aug
Comfy room with private bathroom
Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (20)
"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!
Florida Vacation with pool fun for families
Dining

Florida Vacation with pool fun for families

9.6 out of 10, Exceptional, (30)
"The place is perfectly located and clean. Loved it "
The price is NZ$590
includes taxes & fees
8 Sept - 9 Sept
Florida Vacation with pool fun for families
Private house with pool Kissimmee/Orlando
Dining

Private house with pool Kissimmee/Orlando

9.8 out of 10, Exceptional, (40)
"The details of the house were as listed. The response with the owners were quick and the location was great. We could definitely come back again. "
The price is NZ$670
includes taxes & fees
29 Aug - 30 Aug
Private house with pool Kissimmee/Orlando
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, (94)
"We had a great time on our family vacation here. The place felt clean and was comfortable. We had a short weekend, but while there we enjoyed our stay. The pool was nice to get into after a long day. Would definitely stay again. "
The price is NZ$819
includes taxes & fees
29 Aug - 30 Aug
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Spacious Vacation Home 20 min from Theme Parks!
Interior

Spacious Vacation Home 20 min from Theme Parks!

9.2 out of 10, Wonderful, (56)
"We had a great time"
The price is NZ$670
includes taxes & fees
28 Aug - 29 Aug
Spacious Vacation Home 20 min from Theme Parks!
Quiet Oasis in Lovely Neighborhood
Pool

Quiet Oasis in Lovely Neighborhood

9.8 out of 10, Exceptional, (147)
"Hosts were wondeful. Nice quiet neighborhood. Our favorite part was definitely the pool. "
The price is NZ$321
includes taxes & fees
19 Aug - 20 Aug
Quiet Oasis in Lovely Neighborhood
Large, beautiful, very comfortable one bedroom on small lake
Outdoor pool, a heated pool

Large, beautiful, very comfortable one bedroom on small lake

10.0 out of 10, Exceptional, (57)
"Great place to stay"
The price is NZ$537
includes taxes & fees
28 Aug - 29 Aug
Large, beautiful, very comfortable one bedroom on small lake
Private Luxury Pool / Smart-home
A heated pool

Private Luxury Pool / Smart-home

9.6 out of 10, Exceptional, (72)
"Closest friends and groomsmen! Had the best time. Loved our room and the kitchen and of course the back yard! "
The price is NZ$583
includes taxes & fees
19 Aug - 20 Aug
Private Luxury Pool / Smart-home
Renovated Peaceful Luxury Walk to Mall Park Publix
Fridge, microwave, oven, stovetop

Renovated Peaceful Luxury Walk to Mall Park Publix

9.4 out of 10, Exceptional, (11)
"Very nice little place walking distance to Advent Health."
The price is NZ$382
includes taxes & fees
17 Sept - 18 Sept
Renovated Peaceful Luxury Walk to Mall Park Publix
Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (67)
"It was exactly what we needed!"
The price is NZ$1,060
includes taxes & fees
19 Aug - 20 Aug
Lakefront 5BR Retreat | Pool, Hot Tub & Lake Views
Perfect King Bed, Pet-Friendly, 15 Min to Disney
Property grounds

Perfect King Bed, Pet-Friendly, 15 Min to Disney

Perfect King Bed, Pet-Friendly, 15 Min to Disney
Kissimmee Modern Room with 2 DBL Beds & Tennis Court
Iron/ironing board, free Internet, bed sheets, wheelchair access

Kissimmee Modern Room with 2 DBL Beds & Tennis Court

9.0 out of 10, Wonderful, (2)
"Hubby had a fishing tournament nearby the stay was nice check in went well there is pretty good places in area for food and drink that was close within walking distance"
The price is NZ$146
includes taxes & fees
18 Aug - 19 Aug
Kissimmee Modern Room with 2 DBL Beds & Tennis Court
Magnificent Room with 2 DBL Beds Close to Must-see Attractions
Iron/ironing board, bed sheets, wheelchair access

Magnificent Room with 2 DBL Beds Close to Must-see Attractions

9.6 out of 10, Exceptional, (15)
"Great spot, clean, affordable"
The price is NZ$146
includes taxes & fees
18 Aug - 19 Aug
Magnificent Room with 2 DBL Beds Close to Must-see Attractions
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

The price is NZ$146
includes taxes & fees
18 Aug - 19 Aug
Royal Park Orlando Modern Room with 2 DBL Beds & Tennis Court
Royal Park Orlando Peaceful Room with 2 DBL Beds and Pool
Iron/ironing board, free Internet, bed sheets, wheelchair access

Royal Park Orlando Peaceful Room with 2 DBL Beds and Pool

9.6 out of 10, Exceptional, (24)
"Easily accessible and close to great attractions. "
The price is NZ$146
includes taxes & fees
18 Aug - 19 Aug
Royal Park Orlando Peaceful Room with 2 DBL Beds and Pool
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Garden Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Darnell and Kaya was very helpful I was having issues with adding my Disney tickets to apple wallet and they help, the breakfast was very good also the check out staff was very nice."
Naresh 2-night trip
Posted 13 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings