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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Home in Kissimmee
Lakefront Villa w/pool 4mi to Walt Disney World
4 bedrooms, 5 beds, 3.5 private bathrooms
4–9 Sept
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4.98 out of 5 average rating, 122 reviews
Guest favourite
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
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
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds
15–20 Feb
Superhost
Home in Davenport
7 Bd/ 5.5 Ba/ Windsor Island Resort (3409 Lw)
7 bedrooms
20–25 Aug
New place to stay
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds
22–27 Aug
5.0 out of 5 average rating, 6 reviews
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds
16–21 Aug
New place to stay
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds
16–21 Aug
New place to stay
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds
23–28 Aug
New place to stay
Guest favourite
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
30 Aug – 4 Sept
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
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Home in Kissimmee
Luxury 4BR | Heated Salt Pool | Mini Golf
4 bedrooms, 7 beds
16–21 Aug
New place to stay
Superhost
Villa in Four Corners
Stunning 8BR Villa with Private Pool & Gameroom
8 bedrooms, 11 beds
13–18 Sept
New place to stay
Top guest favourite
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
2 bedrooms, 5 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 11 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
2–7 Oct
New place to stay
Guest favourite
Townhouse in Kissimmee
Upstay Modern Home Near Disney with Pool
4 bedrooms, 5 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Townhouse in Kissimmee
3 Bd/ 3 Ba/ The Hub At Westside (3349 Tt)
3 bedrooms, 5 beds
22–27 Aug
4.89 out of 5 average rating, 9 reviews
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds
17–22 Aug
New place to stay
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 11 reviews