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Search results; Over 1,000 homes in Kissimmee

Descriptions are based on details hosts provide
Top guest favourite
Home in Kissimmee
Heated Pool 15 Minutes to Disney PS5 l Switch
4 bedrooms, 11 beds, 3 private bathrooms
22–27 Aug
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4.99 out of 5 average rating, 165 reviews
Superhost
Home in Kissimmee
Pool home with game room near Disney
7 bedrooms, 6 single beds, 4.5 bathrooms
31 Jul – 5 Aug
New place to stay
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
9 bedrooms, 12 beds, 6 bathrooms
1–6 Aug
New place to stay
Superhost
Home in Kissimmee
Private pool and spa near Disney
6 bedrooms, 6 beds, 5.5 bathrooms
20–25 Aug
New place to stay
Superhost
Townhouse in Davenport
Private pool, minutes from Disney World
4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
New place to stay
Superhost
Home in Kissimmee
Gated home with a private screened pool
5 bedrooms, 7 beds, 5 bathrooms
19–24 Jul
Home in Kissimmee
Themed bedrooms, pool, and golf course views
6 bedrooms, 10 beds, 5 bathrooms
27 Jul – 1 Aug
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
Home in Kissimmee
Private pool and game room near Disney
4 bedrooms, 6 beds, 3 bathrooms
13–18 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Orlando
Themed villa with pool and game room
5 bedrooms, 7 beds, 5 bathrooms
1–6 Sept
Guest favourite
Home in Kissimmee
Newly renovated with a pool, near Disney
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 reviews
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
Home in Kissimmee
5BR Fantastic Villa Pool & Game Room Near Disney
5 bedrooms, 7 beds, 4 bathrooms
11–16 Aug
New place to stay
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
4.97 out of 5 average rating, 36 reviews
Superhost
Home in Kissimmee
Private pool and game room near Disney
7 bedrooms, 9 beds, 6.5 bathrooms
20–25 Jul
New place to stay
Superhost
Home in Kissimmee
Storey Lake Retreat | Private Pool w/ Spa + BBQ
5 bedrooms, 7 beds, 5 bathrooms
9–14 Nov
New place to stay
Home in Kissimmee
Modern villa with a pool near Disney
7 bedrooms, 9 beds, 6.5 bathrooms
15–20 Jul
New place to stay
Superhost
Home in Kissimmee
Screened-in pool, 7.5 miles from Disney
7 bedrooms, 10 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Kissimmee
Private pool and spa near Disney
5 bedrooms, 9 beds, 4.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 5 reviews