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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
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4.9 out of 5 average rating, 105 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
New place to stay, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
5.0 out of 5 average rating, 4 reviews, 1 bed, 1 bathroom
22–27 Jul
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
4.97 out of 5 average rating, 36 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
4.96 out of 5 average rating, 48 reviews, 2 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
4.96 out of 5 average rating, 24 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul
Top guest favourite
Room in Ocoee
Updated 1 bedroom/ 1 bathroom
5.0 out of 5 average rating, 30 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Clermont
Modern & Cozy Studio-Apartment
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 2 beds, 1 bathroom
21–26 Jul
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
12–17 Oct
Top guest favourite
Townhouse in Clermont
Home for 2! Heated Pool, Private Patio, Queen Bed
5.0 out of 5 average rating, 20 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
Top guest favourite
Apartment in Kissimmee
New! Seven Eagles Hideaway at Reunion Resort
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Aug
Top guest favourite
Flat in Orlando
Retreat Luxury Fully Renovated 2026 / Free Shuttle
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Superhost
Townhouse in Davenport
3BD/2.5BATH Family Getaway in a Prime Location
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
27 Jul – 1 Aug
Superhost
Room in Davenport
Suite in Villa|Private Bath|Pool&Spa|Disney
New place to stay, 1 queen bed, 1 bathroom
21–26 Jul
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
5.0 out of 5 average rating, 134 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
31 Aug – 5 Sept