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
$1,372 SGD
Show price breakdown
for 5 nights
$1,372 SGD for 5 nights
,
·
4.99 out of 5 average rating, 197 reviews
4.99 (197)
Guest favourite
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 7 reviews
5.0 (7)
,
·
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4.5 bathrooms
4.5 bathrooms
30 Sept – 5 Oct
30 Sept – 5 Oct
$1,764 SGD
$1,482 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
4.99 out of 5 average rating, 116 reviews
4.99 (116)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
$1,812 SGD
Show price breakdown
for 5 nights
$1,812 SGD for 5 nights
Guest favourite
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
5.0 out of 5 average rating, 9 reviews
5.0 (9)
,
·
7 bedrooms
7 bedrooms
,
·
10 beds
10 beds
,
·
5.5 bathrooms
5.5 bathrooms
5–10 Aug
5–10 Aug
$3,662 SGD
$3,021 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Guest house in Winter Garden
A place with a view
4.9 out of 5 average rating, 104 reviews
4.9 (104)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
3–8 Aug
3–8 Aug
$913 SGD
Show price breakdown
for 5 nights
$913 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
5.0 out of 5 average rating, 7 reviews
5.0 (7)
,
·
6 bedrooms
6 bedrooms
,
·
10 beds
10 beds
,
·
4 bathrooms
4 bathrooms
19–24 Jul
19–24 Jul
$1,756 SGD
$1,399 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 11 reviews
5.0 (11)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
23–28 Jul
23–28 Jul
$1,919 SGD
$1,687 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4.9 out of 5 average rating, 20 reviews
4.9 (20)
,
·
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
4.5 bathrooms
4.5 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$1,280 SGD
$1,128 SGD
Show price breakdown
for 5 nights
Superhost
Superhost
Home in Clermont
Family Fun House at Windsor Cay
New place to stay
New
,
·
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4.5 bathrooms
4.5 bathrooms
26–31 Jul
26–31 Jul
$1,581 SGD
$1,459 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 18 reviews
5.0 (18)
,
·
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
5.5 bathrooms
5.5 bathrooms
26–31 Jul
26–31 Jul
$2,773 SGD
$2,289 SGD
Show price breakdown
for 5 nights
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
$1,996 SGD
$1,541 SGD
Show price breakdown
for 5 nights
Superhost
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
4 bathrooms
4 bathrooms
1–6 Aug
1–6 Aug
$1,603 SGD
Show price breakdown
for 5 nights
$1,603 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
4.98 out of 5 average rating, 83 reviews
4.98 (83)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
8–13 Aug
8–13 Aug
$1,017 SGD
$921 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 92 reviews
4.91 (92)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
19–24 Jul
19–24 Jul
$2,274 SGD
Show price breakdown
for 5 nights
$2,274 SGD for 5 nights
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
6–11 Sept
6–11 Sept
$1,367 SGD
$1,265 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
4.97 out of 5 average rating, 36 reviews
4.97 (36)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
25–30 Aug
25–30 Aug
$1,081 SGD
$918 SGD
Show price breakdown
for 5 nights
Superhost
Superhost
Home in Clermont
Family pool home w/ game room near Disney
5.0 out of 5 average rating, 4 reviews
5.0 (4)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$1,528 SGD
$1,388 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 78 reviews
4.99 (78)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$1,781 SGD
$1,212 SGD
Show price breakdown
for 5 nights
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
New place to stay
New
,
·
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4 bathrooms
4 bathrooms
2–7 Aug
2–7 Aug
$1,538 SGD
Show price breakdown
for 5 nights
$1,538 SGD for 5 nights
1
2
3
4
…
15