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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
,
4.89 out of 5 average rating, 113 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds
14–19 Sept
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 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds
16–21 Aug
New place to stay
Superhost
Home in Four Corners
8BR house sleeps 20 near Disney attractions
8 bedrooms, 8 beds
17–22 Aug
New place to stay
Superhost
Home in Davenport
3BR Luxury Disney Escape | Hot Tub & 2 King Suites
3 bedrooms, 3 beds
15–20 Aug
New place to stay
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
31 Oct – 5 Nov
New place to stay
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
Superhost
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
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds
24–29 Oct
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
31 Aug – 5 Sept
Guest favourite
Townhouse in Kissimmee
Magic Village 4 Suites w/ Jacuzzi - 7493
4 bedrooms, 7 beds
14–19 Aug
4.88 out of 5 average rating, 85 reviews
Superhost
Flat in Kissimmee
3 Bd/ 2 Ba/ Storey Lake (3141-308 Pc)
3 bedrooms, 5 beds
13–18 Aug
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds
5–10 Oct
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds
13–18 Sept
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Townhouse in Kissimmee
5 Bd/ 4 Ba/ Storey Lake (4810 Sq. ft.)
5 bedrooms, 7 beds
25–30 Aug
5.0 out of 5 average rating, 5 reviews
Home in Kissimmee
Superhero HQ: Private Pool & Spa Near Disney
5 bedrooms, 6 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews