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Search results; Over 1,000 homes in Winter Garden

Hotel in Winter Garden
Rare Gem! Outdoor Pool, Kitchenette, Pets Allowed!
1 bedroom, 2 beds, 1 private bathroom
29 Aug – 3 Sept
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5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
23–28 Aug
4.92 out of 5 average rating, 95 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
22–27 Aug
4.9 out of 5 average rating, 58 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
25–30 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds
30 Nov – 5 Dec
4.98 out of 5 average rating, 47 reviews
Guest favourite
Flat in Clermont
Modern & Cozy Studio-Apartment
1 bedroom, 2 beds
25–30 Aug
5.0 out of 5 average rating, 11 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Rooms in Apopka
Spacious close to everything Orlando has to offer
4 bedrooms, 4 beds
21–26 Aug
New place to stay
Top guest favourite
Apartment in Orlando
Super Mario's Sky Suite - Epic Universe 3 BD SUITE
3 bedrooms, 4 beds
28 Aug – 2 Sept
4.95 out of 5 average rating, 189 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds
13–18 Sept
New place to stay
Superhost
Home in Four Corners
8BR house with private pool and game room
8 bedrooms, 8 beds
24–29 Aug
New place to stay
Superhost
Home in Kissimmee
Luxury Villa /Movie Theater/Pool Heater/
3 bedrooms, 5 beds
31 Aug – 5 Sept
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
31 Oct – 5 Nov
New place to stay
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds
21–26 Aug
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds
23–28 Nov
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
24–29 Aug
5.0 out of 5 average rating, 64 reviews
Home in Clermont
25 miles to Disney Contry side house
4 bedrooms, 3 beds
24–29 Aug
New place to stay
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 10 reviews