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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Cottage in Kissimmee
Family Friendly Resort:2/2 Private Patio - Disney!
2 bedrooms, 3 beds, 2 private bathrooms
30 Sept – 5 Oct
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4.96 out of 5 average rating, 230 reviews
Superhost
Home in Four Corners
8 Bd/ 6 Ba/ Windsor Cay (1025 Bw)
8 bedrooms, 8 beds, 6 bathrooms
6–11 Sept
Superhost
Home in Four Corners
8 BD/ 5.5 BA/ Windsor Cay (1016 BW)
8 bedrooms, 13 beds, 5.5 bathrooms
15–20 Sept
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Davenport
Luxury 7-BD Villa - Pool, Theater, and Game Room
7 bedrooms, 14 beds, 5.5 bathrooms
7–12 Sept
New place to stay
Superhost
Home in Kissimmee
2026 Brand New Themed 06 Bedrooms At Solara Resort
6 bedrooms, 2 beds, 5 bathrooms
25–30 Sept
Home in Kissimmee
Luxury Themed Retreat | Private Pool | 4mi-Disney
3 bedrooms, 6 beds, 2.5 bathrooms
6–11 Sept
New place to stay
Superhost
Home in Kissimmee
Luxury Villa /Movie Theater/Pool Heater/
3 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
Superhost
Home in Davenport
Remodeled 5BR | Pool, Theater & Themed Rooms
5 bedrooms, 7 beds, 5.5 bathrooms
13–18 Sept
New place to stay
Superhost
Flat in Orlando
Kids friendly 3 bedroom Condo - Tourist location
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Superhost
Townhouse in Kissimmee
3 Bd/ 3 Ba/ The Hub At Westside (3228 Tt)
3 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds, 5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds, 8 bathrooms
13–18 Sept
Superhost
Home in Kissimmee
Amazing Villa 9Bdrm/Games Room at Solara Resort
9 bedrooms, 12 beds, 6.5 bathrooms
13–18 Sept
Superhost
Flat in Kissimmee
3 Bd/ 2 Ba/ Storey Lake (3141-308 Pc)
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
Superhost
Home in Kissimmee
7 Bd/ 6 Ba/ Storey Lake (4585 Tb)
7 bedrooms, 10 beds, 6 bathrooms
1–6 Oct
New place to stay
Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
4.98 out of 5 average rating, 41 reviews
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Kissimmee
Luxury Reunion Retreat Patio Views Near Disney
5 bedrooms, 6 beds, 4 bathrooms
2–7 Sept
New place to stay