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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Apartment in Kissimmee
Disney Themed Condo 5 Miles to Disney World
2 bedrooms, 4 beds, 2 private bathrooms
29 Jun – 4 Jul
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4.89 out of 5 average rating, 113 reviews
Guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
29 Aug – 3 Sept
New place to stay
Superhost
Home in Kissimmee
7 Bd/5.5Ba Sleeps 16! Windsor at Westside (2100RD)
7 bedrooms, 9 beds, 5.5 bathrooms
1–6 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
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds, 4 bathrooms
30 Jul – 4 Aug
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Home in Kissimmee
Magical Villa with Themed Bedrooms at Reunion
6 bedrooms, 10 beds, 5 bathrooms
27 Jul – 1 Aug
New place to stay
Superhost
Townhouse in Kissimmee
5BR Waterfront Townhome w/ Pool Near Bronson Club
5 bedrooms, 6 beds, 4 bathrooms
30 Jul – 4 Aug
New place to stay
Top guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds, 4 bathrooms
7–12 Feb
5.0 out of 5 average rating, 6 reviews
Home in Kissimmee
8BR/6BA Magical Themed LakeView HotTub Near Disney
8 bedrooms, 11 beds, 6 bathrooms
4–9 Aug
New place to stay
Home in Kissimmee
Lakefront Charmer 8BR 6BA Home Cinema Pool/Spa
8 bedrooms, 13 beds, 6 bathrooms
26–31 Jul
New place to stay
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 bedrooms, 9 beds, 4.5 bathrooms
5–10 Jan
5.0 out of 5 average rating, 14 reviews
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
New place to stay
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
5 bedrooms, 8 beds, 3.5 bathrooms
29 Jul – 3 Aug
New place to stay
Guest favourite
Home in Davenport
Peaceful 4BR Pool Villa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds, 4.5 bathrooms
2–7 Aug
4.9 out of 5 average rating, 20 reviews