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Search results; Over 1,000 homes in Kissimmee

Apartment in Kissimmee
Retreat Golf View & Amazing Pools Near Disney
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
,
4.78 out of 5 average rating, 240 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
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
28 Aug – 2 Sept
Superhost
Home in Kissimmee
8 Bedrooms/ 5 Bathrooms/ Storey Lake (4582NL)
8 bedrooms, 12 beds
3–8 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 10 reviews
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
10 bedrooms, 14 beds
14–19 Aug
New place to stay
Flat in Kissimmee
Family Vacation Condo with pool/20 Min from Disney
3 bedrooms, 4 beds
7–12 Aug
New place to stay
Guest favourite
Home in Kissimmee
7 BD/ 7 BA/ Solara Resort (2327 SR)
7 bedrooms, 10 beds
18–23 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
3 bedrooms, 4 beds
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
16–21 Aug
New place to stay
Superhost
Home in Kissimmee
7BR/6BA w/ Private Pool | Solara Resort (SO9051)
7 bedrooms, 11 beds
17–22 Aug
New place to stay
Guest favourite
Home in Davenport
Home Away from Home + 2 suites
5 bedrooms, 6 beds
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
2–7 Aug
New place to stay
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
9 bedrooms, 12 beds
31 Aug – 5 Sept
New place to stay
Home in Kissimmee
Poolside Heaven in Cumbrian Lakes
4 bedrooms, 6 beds
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in Kissimmee
4 BD/ 3 BA/ Storey Lake (4285 QS)
4 bedrooms, 5 beds
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds
15–20 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Clermont
10 BD/ 8 BA/ Windsor Cay (1018 CR)
10 bedrooms, 18 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms, 7 beds
19–24 Aug
5.0 out of 5 average rating, 20 reviews