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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, 198 reviews
Home in Ocoee
Serenity Retreat
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Superhost
Flat in Orlando
Luxury 1BR & Resort Amenities + 6min to Epic-Unive
New place to stay, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Ocoee
Quiet Comfy Apartment Orlando Area
4.83 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Aug
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
5.0 out of 5 average rating, 4 reviews, 1 bed, 1 bathroom
1–6 Aug
Room in Ocoee
Bedroom and private bathroom
New place to stay, 1 queen bed, 1.5 bathrooms
7–12 Aug
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
1–6 Aug
Guest favourite
Flat in Kissimmee
8050-112 Luxury 2BR Apt Kissimmee Orlando Disney
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Superhost
Flat in Orlando
Luxury 1BR & Resort Amenities - 6min to Epic-Uni
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Aug
Top guest favourite
Room in Orlando
Cozy Private suite near OCC and Epic Universal
5.0 out of 5 average rating, 17 reviews, 1 bed, 1 bathroom
8–13 Aug
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
4.98 out of 5 average rating, 62 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Aug
Superhost
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
Top guest favourite
Townhouse in Clermont
House for 2! Heated Pool, Private Patio, Queen Bed
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Sept
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
4.97 out of 5 average rating, 37 reviews, 3 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
Guest favourite
Flat in Orlando
King Bed Haven, Amazing Pool, Gym, & Pet-Friendly
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Orlando
Top5% VillaTerracotta: Boho Chic |FreeParkShuttle
5.0 out of 5 average rating, 77 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 Aug