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
Guest favourite
Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom
,
·
1 bed
,
·
1 private bathroom
2–7 Aug
2–7 Aug
$1,100 SGD
Show price breakdown
for 5 nights
$1,100 SGD for 5 nights
,
·
4.92 out of 5 average rating, 225 reviews
4.92 (225)
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
$1,834 SGD
Show price breakdown
for 5 nights
$1,834 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
5–10 Aug
5–10 Aug
$2,278 SGD
Show price breakdown
for 5 nights
$2,278 SGD for 5 nights
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
$2,957 SGD
$2,495 SGD
Show price breakdown
for 5 nights
Book early to save
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
28 Aug – 2 Sept
28 Aug – 2 Sept
$2,516 SGD
$2,138 SGD
Show price breakdown
for 5 nights
Book early to save
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4 bathrooms
4 bathrooms
16–21 Aug
16–21 Aug
$1,557 SGD
$1,305 SGD
Show price breakdown
for 5 nights
New place to stay
New
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$1,002 SGD
$854 SGD
Show price breakdown
for 5 nights
New place to stay
New
Flat in Kissimmee
Family Vacation Condo with pool/20 Min from Disney
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
9–14 Aug
9–14 Aug
$970 SGD
Show price breakdown
for 5 nights
$970 SGD for 5 nights
New place to stay
New
Room in Ocoee
Bedroom and private bathroom
1 queen bed
1 queen bed
,
·
1.5 bathrooms
1.5 bathrooms
7–12 Aug
7–12 Aug
$317 SGD
Show price breakdown
for 5 nights
$317 SGD for 5 nights
New place to stay
New
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
$1,685 SGD
Show price breakdown
for 5 nights
$1,685 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$750 SGD
Show price breakdown
for 5 nights
$750 SGD for 5 nights
4.97 out of 5 average rating, 38 reviews
4.97 (38)
Superhost
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4.5 bathrooms
4.5 bathrooms
16–21 Aug
16–21 Aug
$1,345 SGD
Show price breakdown
for 5 nights
$1,345 SGD for 5 nights
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
$2,032 SGD
$1,676 SGD
Show price breakdown
for 5 nights
Extended stay discount
5.0 out of 5 average rating, 13 reviews
5.0 (13)
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
$1,336 SGD
$1,240 SGD
Show price breakdown
for 5 nights
Book early to save
New place to stay
New
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
$873 SGD
Show price breakdown
for 5 nights
$873 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Apartment in Kissimmee
*NEW* 3BR/2BA Condo w/ pool, steps to Disney
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Aug
1–6 Aug
$919 SGD
$827 SGD
Show price breakdown
for 5 nights
New place to stay
New
Superhost
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms
12 bedrooms
,
·
24 beds
24 beds
,
·
15 bathrooms
15 bathrooms
5–10 Aug
5–10 Aug
$21,391 SGD
$17,262 SGD
Show price breakdown
for 5 nights
New place to stay
New
Home in Kissimmee
The Magical Wizard's Hideaway
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
2–7 Aug
2–7 Aug
$1,227 SGD
Show price breakdown
for 5 nights
$1,227 SGD for 5 nights
New place to stay
New
Townhouse in Davenport
Beautiful townhouse just 15 minutes from Disney
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
15–20 Aug
15–20 Aug
$1,241 SGD
$1,055 SGD
Show price breakdown
for 5 nights
New place to stay
New
1
2
3
4
…
15