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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Apartment in Kissimmee
Fireworks Penthouse: Top Floor, Star Wars, 2 Pools
3 bedrooms, 4 beds, 2 private bathrooms
1–6 Oct
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4.96 out of 5 average rating, 181 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
14–19 Feb
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
10 bedrooms, 14 beds, 8 bathrooms
14–19 Aug
New place to stay
Superhost
Home in Kissimmee
8 Bedrooms/ 5 Bathrooms/ Storey Lake (4582NL)
8 bedrooms, 12 beds, 5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct
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, 10 reviews
Guest favourite
Home in Davenport
Home Away from Home + 2 suites
5 bedrooms, 6 beds, 3 bathrooms
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
9 bedrooms, 12 beds, 6 bathrooms
31 Aug – 5 Sept
New place to stay
Guest favourite
Home in Kissimmee
7 BD/ 7 BA/ Solara Resort (2327 SR)
7 bedrooms, 10 beds, 6.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 5 reviews
Home in Kissimmee
Golden Haven | 14 PPL | Pool | 12 Min to Disney
5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Flat in Kissimmee
Family Vacation Condo with pool/20 Min from Disney
2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
New place to stay
Top guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
3 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
4.91 out of 5 average rating, 11 reviews
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
10 bedrooms, 14 beds, 8 bathrooms
16–21 Aug
New place to stay
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds, 6.5 bathrooms
1–6 Aug
New place to stay
Home in Kissimmee
Poolside Heaven in Cumbrian Lakes
4 bedrooms, 6 beds, 3 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Chic 8BR All Suites with Pool and Game Room
8 bedrooms, 10 beds, 8 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds, 3 bathrooms
15–20 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds, 2.5 bathrooms
2–7 Aug
New place to stay