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Homes in Winter Garden
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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
$1,337 SGD
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for 5 nights
$1,337 SGD for 5 nights
,
·
4.99 out of 5 average rating, 198 reviews
4.99 (198)
Home in Ocoee
Serenity Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
10–15 Aug
10–15 Aug
$1,062 SGD
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for 5 nights
$1,062 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
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
$749 SGD
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for 5 nights
$749 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 38 reviews
4.97 (38)
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
$952 SGD
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for 5 nights
$952 SGD for 5 nights
Pay $0 today
Free cancellation
4.89 out of 5 average rating, 55 reviews
4.89 (55)
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
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for 5 nights
$317 SGD for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
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
1–6 Sept
1–6 Sept
$1,106 SGD
$1,011 SGD
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for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Ocoee
Quiet Comfy Apartment Orlando Area
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
11–16 Aug
11–16 Aug
$691 SGD
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for 5 nights
$691 SGD for 5 nights
Free cancellation
4.83 out of 5 average rating, 113 reviews
4.83 (113)
Top guest favourite
Guest favourite
Flat in Orlando
Modern Oasis | King Bed • Pool & Gym • Near Epic U
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,107 SGD
$898 SGD
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for 5 nights
Extended stay discount
5.0 out of 5 average rating, 61 reviews
5.0 (61)
Superhost
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed
1 bed
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$594 SGD
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for 5 nights
$594 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$659 SGD
$594 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 24 reviews
4.96 (24)
Top guest favourite
Guest favourite
Flat in Orlando
Retreat Luxury Fully Renovated 2026 / Free Shuttle
1 bedroom
1 bedroom
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$1,099 SGD
$953 SGD
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for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Top guest favourite
Guest favourite
Townhouse in Clermont
House for 2! Heated Pool, Private Patio, Queen Bed
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$811 SGD
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for 5 nights
$811 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Top guest favourite
Guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
25–30 Aug
25–30 Aug
$727 SGD
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for 5 nights
$727 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 61 reviews
4.98 (61)
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
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for 5 nights
Book early to save
Pay $0 today
Free cancellation
New place to stay
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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
10–15 Aug
10–15 Aug
$1,724 SGD
$1,450 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.89 out of 5 average rating, 9 reviews
4.89 (9)
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
26–31 Aug
26–31 Aug
$2,526 SGD
$2,147 SGD
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for 5 nights
Book early to save
Pay $0 today
Free cancellation
Superhost
Superhost
Apartment in Kissimmee
9-201 Legacy Dunes, Heated Pool. Close to Disney
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Aug
1–6 Aug
$889 SGD
$806 SGD
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for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Flat in Winter Park
The Grove
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$559 SGD
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for 5 nights
$559 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Room in St. Cloud
Peaceful private room
1 bed
1 bed
,
·
WC
WC
1–6 Jan
1–6 Jan
$185 SGD
$153 SGD
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for 5 nights
Pay $0 today
Free cancellation
New place to stay
New
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