Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Winter Garden
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Winter Garden
Over 1,000 homes in Winter Garden
Top guest favourite
Guest favourite
Cottage in Winter Garden
The Heart of Winter Garden: Walk to shops & dining
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
9–14 Sept
9–14 Sept
$1,336 SGD
Show price breakdown
for 5 nights
$1,336 SGD for 5 nights
,
·
4.99 out of 5 average rating, 198 reviews
4.99 (198)
Top guest favourite
Guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Aug
1–6 Aug
$1,671 SGD
Show price breakdown
for 5 nights
$1,671 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Top guest favourite
Guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Aug
1–6 Aug
$2,275 SGD
Show price breakdown
for 5 nights
$2,275 SGD for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 93 reviews
4.91 (93)
Superhost
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms
10 bedrooms
,
·
16 beds
16 beds
,
·
8 bathrooms
8 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$2,964 SGD
$2,500 SGD
Show price breakdown
for 5 nights
Book early to save
Pay $0 today
Free cancellation
New place to stay
New
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$1,334 SGD
$1,239 SGD
Show price breakdown
for 5 nights
Book early to save
New place to stay
New
Top guest favourite
Guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
8–13 Aug
8–13 Aug
$2,029 SGD
$1,674 SGD
Show price breakdown
for 5 nights
Extended stay discount
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Superhost
Superhost
Home in Kissimmee
Jungle pool home w/ hot tub - close to Disney
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
17–22 Aug
17–22 Aug
$1,309 SGD
$1,118 SGD
Show price breakdown
for 5 nights
New place to stay
New
Superhost
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
5 bathrooms
5 bathrooms
2–7 Aug
2–7 Aug
$1,549 SGD
Show price breakdown
for 5 nights
$1,549 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
Superhost
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
5 bathrooms
5 bathrooms
16–21 Aug
16–21 Aug
$1,768 SGD
Show price breakdown
for 5 nights
$1,768 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
23–28 Aug
23–28 Aug
$904 SGD
Show price breakdown
for 5 nights
$904 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 25 reviews
5.0 (25)
Superhost
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
5.5 bathrooms
5.5 bathrooms
20–25 Sept
20–25 Sept
$1,691 SGD
Show price breakdown
for 5 nights
$1,691 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Home in Kissimmee
Sleeps 13-Park Shuttle-Themed Rooms-Solara Resort
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
5.5 bathrooms
5.5 bathrooms
1–6 Aug
1–6 Aug
$3,056 SGD
$2,780 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
Superhost
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms
7 bedrooms
,
·
8 single beds
8 single beds
,
·
5 bathrooms
5 bathrooms
6–11 Aug
6–11 Aug
$2,662 SGD
$2,257 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
12–17 Sept
12–17 Sept
$1,549 SGD
$1,132 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Guest favourite
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms
6 bedrooms
,
·
9 beds
9 beds
,
·
3 bathrooms
3 bathrooms
13–18 Aug
13–18 Aug
$2,490 SGD
$1,724 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Superhost
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
10 bedrooms
10 bedrooms
,
·
14 beds
14 beds
,
·
8 bathrooms
8 bathrooms
9–14 Aug
9–14 Aug
$4,949 SGD
$3,704 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
3.5 bathrooms
3.5 bathrooms
1–6 Aug
1–6 Aug
$1,863 SGD
Show price breakdown
for 5 nights
$1,863 SGD for 5 nights
Free cancellation
New place to stay
New
Home in Davenport
Modern 4BR w/ Private Pool - Minutes from Disney
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
8–13 Aug
8–13 Aug
$1,357 SGD
Show price breakdown
for 5 nights
$1,357 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
11–16 Aug
11–16 Aug
$1,332 SGD
Show price breakdown
for 5 nights
$1,332 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
1
2
3
4
…
15