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Search results; Over 1,000 homes in Kissimmee

Superhost
Villa in Kissimmee
Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE
8 bedrooms, 10 beds, 4.5 private bathrooms
11–16 Oct
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4.85 out of 5 average rating, 257 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds
14–19 Sept
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
2–7 Oct
New place to stay
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds
16–21 Aug
New place to stay
Superhost
Home in Four Corners
2026 BRAND NEW 08BD At Windsor Cay
8 bedrooms, 8 beds
15–20 Aug
New place to stay
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds
11–16 Aug
New place to stay
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Four Corners
8 Bd/ 6 Ba/ Windsor Cay (1025 Bw)
8 bedrooms, 8 beds
19–24 Aug
Home in Kissimmee
5Bed/4Bath Luxurious Privacy
5 bedrooms, 6 beds
16–21 Aug
New place to stay
Superhost
Home in Kissimmee
2026 6BR Themed Home w/ LED Pool at Solara Resort
6 bedrooms, 8 beds
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds
30 Aug – 4 Sept
Home in Kissimmee
Simply Magical | 13 PPL | Pool | Mini Golf | Games
4 bedrooms, 6 beds
19–24 Aug
New place to stay
Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 40 reviews
Superhost
Home in Kissimmee
9BR Pixar Theater Game Room | Pool Spa | Sleeps 27
9 bedrooms, 19 beds
11–16 Aug
New place to stay
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds
31 Aug – 5 Sept
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
Superhost
Flat in Kissimmee
3 Bd/ 2 Ba/ Storey Lake (3141-308 Pc)
3 bedrooms, 5 beds
11–16 Aug
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds
15–20 Aug
New place to stay