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
$1,102 SGD
Show price breakdown
for 5 nights
$1,102 SGD for 5 nights
,
·
4.92 out of 5 average rating, 224 reviews
4.92 (224)
Guest favourite
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4.5 bathrooms
4.5 bathrooms
30 Jul – 4 Aug
30 Jul – 4 Aug
$1,805 SGD
Show price breakdown
for 5 nights
$1,805 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
16–21 Jul
16–21 Jul
$2,019 SGD
Show price breakdown
for 5 nights
$2,019 SGD for 5 nights
4.99 out of 5 average rating, 116 reviews
4.99 (116)
Top guest favourite
Guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$937 SGD
$840 SGD
Show price breakdown
for 5 nights
4.89 out of 5 average rating, 55 reviews
4.89 (55)
Superhost
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$1,552 SGD
$1,393 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
23–28 Jul
23–28 Jul
$1,925 SGD
$1,693 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
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
21–26 Jul
21–26 Jul
$707 SGD
Show price breakdown
for 5 nights
$707 SGD for 5 nights
4.97 out of 5 average rating, 34 reviews
4.97 (34)
Top guest favourite
Guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
28 Jul – 2 Aug
28 Jul – 2 Aug
$1,145 SGD
Show price breakdown
for 5 nights
$1,145 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
29 Jul – 3 Aug
29 Jul – 3 Aug
$1,000 SGD
Show price breakdown
for 5 nights
$1,000 SGD for 5 nights
4.98 out of 5 average rating, 83 reviews
4.98 (83)
Superhost
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms
7 bedrooms
,
·
6 single beds
6 single beds
,
·
4.5 bathrooms
4.5 bathrooms
31 Jul – 5 Aug
31 Jul – 5 Aug
$2,670 SGD
Show price breakdown
for 5 nights
$2,670 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
$2,026 SGD
$1,625 SGD
Show price breakdown
for 5 nights
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$1,295 SGD
Show price breakdown
for 5 nights
$1,295 SGD 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
19–24 Jul
19–24 Jul
$2,282 SGD
Show price breakdown
for 5 nights
$2,282 SGD for 5 nights
4.91 out of 5 average rating, 92 reviews
4.91 (92)
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
$1,371 SGD
$1,270 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Home in Clermont
8 BD/ 6 BA / Windsor Cay (15989 CC)
8 bedrooms
8 bedrooms
,
·
12 beds
12 beds
,
·
6 bathrooms
6 bathrooms
6–11 Sept
6–11 Sept
$2,137 SGD
$1,938 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Superhost
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
3–8 Aug
3–8 Aug
$1,014 SGD
Show price breakdown
for 5 nights
$1,014 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
15–20 Aug
15–20 Aug
$3,210 SGD
$2,954 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
1–6 Aug
1–6 Aug
$1,774 SGD
Show price breakdown
for 5 nights
$1,774 SGD for 5 nights
New place to stay
New
Superhost
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4.5 bathrooms
4.5 bathrooms
11–16 Aug
11–16 Aug
$1,569 SGD
Show price breakdown
for 5 nights
$1,569 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
1
2
3
4
…
15