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Search results; Over 1,000 homes in Winter Garden

Top 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
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4.99 out of 5 average rating, 199 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 95 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
19–24 Aug
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
20–25 Aug
4.9 out of 5 average rating, 58 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 105 reviews
Top guest favourite
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 4 reviews
Rooms in Apopka
Spacious close to everything Orlando has to offer
4 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
New place to stay
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Nov
4.97 out of 5 average rating, 33 reviews
Guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
30 Nov – 5 Dec
4.98 out of 5 average rating, 47 reviews
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Davenport
The Ultimate Family Getaway Near Disney
3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Guest house in Orlando
Guest Home-Orlando Airport and Disney-Free Parking
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Davenport
Remodeled 5BR | Pool, Theater & Themed Rooms
5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Aug
New place to stay
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
15–20 Feb