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
$1,092 SGD
Show price breakdown
for 5 nights
$1,092 SGD for 5 nights
,
·
4.92 out of 5 average rating, 225 reviews
4.92 (225)
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
$994 SGD
$847 SGD
Show price breakdown
for 5 nights
New place to stay
New
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
$2,260 SGD
Show price breakdown
for 5 nights
$2,260 SGD for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 93 reviews
4.91 (93)
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
3–8 Aug
3–8 Aug
$735 SGD
Show price breakdown
for 5 nights
$735 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 39 reviews
4.97 (39)
Top guest favourite
Guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$934 SGD
$869 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.89 out of 5 average rating, 56 reviews
4.89 (56)
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
$315 SGD
Show price breakdown
for 5 nights
$315 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
Home in Ocoee
Serenity Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
10–15 Aug
10–15 Aug
$971 SGD
Show price breakdown
for 5 nights
$971 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
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
$1,819 SGD
Show price breakdown
for 5 nights
$1,819 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
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
12–17 Oct
12–17 Oct
$3,141 SGD
$2,641 SGD
Show price breakdown
for 5 nights
Book early to save
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
28 Aug – 2 Sept
28 Aug – 2 Sept
$2,537 SGD
$2,239 SGD
Show price breakdown
for 5 nights
Book early to save
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in Clermont
Stunning 5B/4.5B, Heated Pool & BBQ
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4.5 bathrooms
4.5 bathrooms
2–7 Aug
2–7 Aug
$1,707 SGD
$1,350 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Top guest favourite
Guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2.5 bathrooms
2.5 bathrooms
18–23 Sept
18–23 Sept
$1,218 SGD
Show price breakdown
for 5 nights
$1,218 SGD for 5 nights
5.0 out of 5 average rating, 80 reviews
5.0 (80)
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
9 bedrooms
9 bedrooms
,
·
20 beds
20 beds
,
·
5 bathrooms
5 bathrooms
9–14 Aug
9–14 Aug
$2,533 SGD
Show price breakdown
for 5 nights
$2,533 SGD for 5 nights
Pay $0 today
Free cancellation
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
$2,015 SGD
$1,663 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
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
$1,334 SGD
Show price breakdown
for 5 nights
$1,334 SGD for 5 nights
New place to stay
New
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
9–14 Aug
9–14 Aug
$993 SGD
Show price breakdown
for 5 nights
$993 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favourite
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
5.5 bathrooms
5.5 bathrooms
19–24 Aug
19–24 Aug
$2,540 SGD
$1,938 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 20 reviews
5.0 (20)
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
$1,666 SGD
Show price breakdown
for 5 nights
$1,666 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
3–8 Aug
3–8 Aug
$1,552 SGD
Show price breakdown
for 5 nights
$1,552 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 27 reviews
5.0 (27)
1
2
3
4
…
15