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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Guest house in Kissimmee
"Little Blue House" Getaway Near the Disney Parks
1 bedroom, 2 beds, 1 private bathroom
6–11 Dec
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4.98 out of 5 average rating, 333 reviews
Guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
4.86 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
7–12 Dec
Superhost
Home in Orlando
Themed 5BR Villa Minutes from Disney & Universal
5 bedrooms, 7 beds, 5 bathrooms
1–6 Sept
Superhost
Home in Kissimmee
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds, 4 bathrooms
30 Jul – 4 Aug
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
Superhost
Home in Kissimmee
7 Bd/5.5Ba Sleeps 16! Windsor at Westside (2100RD)
7 bedrooms, 9 beds, 5.5 bathrooms
1–6 Aug
Home in Kissimmee
Magical Villa with Themed Bedrooms at Reunion
New place to stay, 6 bedrooms, 10 beds, 5 bathrooms
27 Jul – 1 Aug
Superhost
Home in Kissimmee
7 BD/ 5.5 BA/ Windsor at Westside (1897 NC)
7 bedrooms, 10 beds, 5.5 bathrooms
3–8 Aug
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds, 4.5 bathrooms
18–23 Jul
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5.0 out of 5 average rating, 14 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
5–10 Jan
Top guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 8 beds, 4 bathrooms
7–12 Feb
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
9–14 Sept
Superhost
Villa in Kissimmee
Star Wars Loft, Themed Rooms, Summer Kitchen & PS5
7 bedrooms, 13 beds, 5.5 bathrooms
3–8 Aug
Superhost
Home in Kissimmee
Pvt Pool&Spa·Game Room·BBQ·Near Theme Parks
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
28 Aug – 2 Sept
Superhost
Home in Kissimmee
5 BD/ 5 BA/ Reunion Village (7852 MP)
5 bedrooms, 7 beds, 5 bathrooms
19–24 Jul
Home in Kissimmee
8BR/6BA Magical Themed LakeView HotTub Near Disney
New place to stay, 8 bedrooms, 11 beds, 6 bathrooms
15–20 Aug
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Superhost
Home in Kissimmee
Storey Lake Retreat | Private Pool w/ Spa + BBQ
New place to stay, 5 bedrooms, 7 beds, 5 bathrooms
9–14 Nov