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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Apartment in Kissimmee
Andy's Toy Chest at Resort Minutes from Disney!
3 bedrooms, 4 beds, 2 private bathrooms
30 Sept – 5 Oct
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4.94 out of 5 average rating, 244 reviews
Townhouse in Davenport
Solterra resort townhouse w/ private pool
4 bedrooms, 5 beds
19–24 Aug
New place to stay
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds
4–9 Aug
New place to stay
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
9–14 Aug
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 Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds
23–28 Aug
Home in Kissimmee
Brisa Family Retreat with Private Pool
3 bedrooms, 4 beds
17–22 Aug
New place to stay
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
7–12 Mar
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Golden Haven | Heated Pool | 7 Beds | Near Disney
5 bedrooms, 7 beds
14–19 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds
5–10 Aug
New place to stay
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds
10–15 Aug
Guest favourite
Home in Kissimmee
Stylish 4BR | Private Pool | Patio | Game Room
4 bedrooms, 4 beds
14–19 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds
14–19 Aug
New place to stay
Superhost
Apartment in Kissimmee
406 - Toy Story & Safari Dream Condo
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 5 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
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds
9–14 Aug
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
10 bedrooms, 14 beds
18–23 Aug
New place to stay