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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Apartment in Kissimmee
Stunning Sunny Central Condo w/ Pool & Balcony
2 bedrooms, 4 beds, 2 private bathrooms
29 Aug – 3 Sept
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4.8 out of 5 average rating, 270 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
2–7 Oct
New place to stay
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds
25–30 Oct
4.9 out of 5 average rating, 10 reviews
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps6, Pool & Gym
2 bedrooms, 3 beds
9–14 Aug
New place to stay
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
23–28 Aug
Guest favourite
Home in Kissimmee
2026 NEW 06 Bedrooms at Solara Resort/Private Pool
6 bedrooms, 9 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Davenport
5 Bd/ 4.5 Ba/ The Enclaves At Festival (450 Cd)
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds
6–11 Aug
New place to stay
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds
23–28 Aug
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds
31 Aug – 5 Sept
New place to stay
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds
14–19 Aug
New place to stay
Guest favourite
Home in Davenport
Mickey Disney Villa | Pool | Arcade | King Suites
4 bedrooms, 6 beds
7–12 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Kissimmee
Stylish 4BR | Private Pool | Patio | Game Room
4 bedrooms, 4 beds
14–19 Aug
5.0 out of 5 average rating, 11 reviews
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds
8–13 Nov
New place to stay
Home in Kissimmee
Brisa Family Retreat with Private Pool
3 bedrooms, 4 beds
13–18 Aug
New place to stay
Superhost
Home in Kissimmee
Luxury NEW 09 Bedroom/Pool At Solara Resort
9 bedrooms, 13 beds
10–15 Aug
5.0 out of 5 average rating, 4 reviews
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