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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Loft in Kissimmee
Mickey 195 Themed Loft
1 bedroom, 2 beds, 1 private bathroom
1–6 Aug
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4.72 out of 5 average rating, 198 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, 11 reviews
Flat in Kissimmee
3BR Townhouse Near Disney Resort Style (8 Guests)
3 bedrooms, 4 beds
1–6 Aug
New place to stay
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
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
9–14 Aug
New place to stay
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
28 Aug – 2 Sept
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
Superhost
Home in Kissimmee
8 Bedrooms/ 5 Bathrooms/ Storey Lake (4582NL)
8 bedrooms, 12 beds
10–15 Sept
5.0 out of 5 average rating, 3 reviews
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
Superhost
Home in Kissimmee
Brand NEW 2026 08 Bedrooms At Solara Resort
8 bedrooms, 11 beds
15–20 Nov
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds
1–6 Aug
New place to stay
Home in Kissimmee
4BR Bright home with private pool
4 bedrooms, 7 beds
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds
17–22 Aug
New place to stay
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
10 bedrooms, 14 beds
16–21 Aug
New place to stay
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds
18–23 Oct
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
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
9 bedrooms, 12 beds
31 Aug – 5 Sept
New place to stay