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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Apartment in Kissimmee
Stunning Sunny Central Condo w/ Pool & Balcony
2 bedrooms, 4 beds, 2 private bathrooms
29 Aug – 3 Sept
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4.8 out of 5 average rating, 270 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
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
9 bedrooms, 20 beds
9–14 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
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
10–15 Sept
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
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
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
3 bedrooms, 4 beds
9–14 Aug
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
Guest favourite
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds
18–23 Oct
Home in Kissimmee
Chic 8BR All Suites with Pool and Game Room
8 bedrooms, 10 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Kissimmee
Cozy nd peaceful home w/ lake, near Disney Parks!
3 bedrooms, 4 beds
16–21 Nov
5.0 out of 5 average rating, 7 reviews
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
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds
16–21 Aug
New place to stay
Superhost
Home in Kissimmee
Themed Coral Cay GEM-Disney 10 min-Free resort/BBQ
4 bedrooms, 6 beds
7–12 Aug
New place to stay
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds
1–6 Aug
New place to stay