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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.91 out of 5 average rating, 223 reviews
Top guest favourite
Villa in Clermont
Villa for 5 - Mins to Mickey, Golf, Pickleball, DT
2 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
4.96 out of 5 average rating, 45 reviews
Superhost
Townhouse in Clermont
Private Pool, BBQ | Steps to Clubhouse
3 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
New place to stay
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
4.97 out of 5 average rating, 34 reviews
Home in Kissimmee
Home Near Disney with pool, theater & games.
3 bedrooms, 5 beds, 1 bathroom
1–6 Jul
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 79 reviews
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Kissimmee
3121 Modern Condo Near Disney | Storey Lake Resort
2 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Clermont
Brand 2026 Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
1–6 Aug
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 23 reviews
Flat in Orlando
King Suite w Pool & Hot Tub Near Disney
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Orlando
3BR Stylish King Family• Pets • Pool • Gym Near Ep
3 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 45 reviews
Guest favourite
Apartment in Orlando
Mickey's House in Orlando • 10 minutes from Disney
1 bedroom, 2 queen beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Clermont
Private pool & hot tub - 19 mins to Disney
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
New place to stay
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds, 4 bathrooms
5–10 Sept
5.0 out of 5 average rating, 5 reviews
Home in Kissimmee
Orlando Vacation Home | Pool + Near Parks
4 bedrooms, 5 beds, 3 bathrooms
13–18 Jul
New place to stay
Guest favourite
Guest house in Orlando
Cozy Guest House Near MCO & Theme Parks
1 bedroom, 2 beds, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Orlando
Tropical Oasis|Lounge|Putting Green|Heated Pool
3 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 5 reviews