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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Winter Garden, Florida
2 bedrooms, 2 beds, 1 private bathroom
22–27 Jul
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4.99 out of 5 average rating, 159 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
21–26 Jul
New place to stay
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed
22–27 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed
28 Jul – 2 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
26–31 Jul
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds
22–27 Jul
4.96 out of 5 average rating, 24 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
12–17 Oct
New place to stay
Top guest favourite
Flat in Clermont
Modern & Cozy Studio-Apartment
1 bedroom, 2 beds
21–26 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Townhouse in Clermont
Home for 2! Heated Pool, Private Patio, Queen Bed
1 bedroom, 1 queen bed
10–15 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Room in Ocoee
Updated 1 bedroom/ 1 bathroom
1 queen bed
1–6 Aug
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds
25–30 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Apartment in Kissimmee
New! Seven Eagles Hideaway at Reunion Resort
1 bedroom, 1 king bed
5–10 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Orlando
Retreat Luxury Fully Renovated 2026 / Free Shuttle
1 bedroom, 2 queen beds
2–7 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Townhouse in Davenport
3BD/2.5BATH Family Getaway in a Prime Location
3 bedrooms, 4 beds
23–28 Jul
New place to stay
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds
2–7 Aug
New place to stay
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed
23–28 Jul
5.0 out of 5 average rating, 134 reviews
Superhost
Room in Davenport
Suite in Villa|Private Bath|Pool&Spa|Disney
1 queen bed
21–26 Jul
New place to stay
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
27 Jul – 1 Aug
4.89 out of 5 average rating, 55 reviews