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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Townhouse in Kissimmee
Townhouse - 5 miles to Disney!
3 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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4.98 out of 5 average rating, 250 reviews
Top guest favourite
Flat in Orlando
Villa Magical by Boho Luxe •Top1% |FreeParkShuttle
1 bedroom, 5 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Kissimmee
Amazing 3Bdrms/2,5bath At Encantada
3 bedrooms, 5 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds, 4.5 bathrooms
1–6 Mar
5.0 out of 5 average rating, 24 reviews
Guest favourite
Townhouse in Kissimmee
Elegant townhouse w/ pool & resort access
5 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Townhouse in Kissimmee
Upstay Modern Home Near Disney with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Home in Kissimmee
NICE 15BR Home Near Disney | Groups Welcome
15 bedrooms, 20 beds, 15 bathrooms
18–23 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 43 reviews
Home in Davenport
The Palm w/ themed rooms private pool near Disney
4 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
New place to stay
Guest favourite
Flat in Kissimmee
Welcome to your Wizarding Adventure
3 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Kissimmee
Immersive 15 Bd/ 16.5 Ba/ Sonoma Resort (4071Sb)
15 bedrooms, 22 beds, 16.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Villa in Kissimmee
Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub
7 bedrooms, 11 beds, 6.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 167 reviews
Superhost
Home in Kissimmee
4BR house with private pool in Magic Village
4 bedrooms, 6 beds, 4.5 bathrooms
13–18 Sept
Superhost
Home in Kissimmee
NEW 2026 Themed 9BR| Racing Simulator |Solara
9 bedrooms, 13 beds, 6.5 bathrooms
20–25 Sept
New place to stay
Luxe
Villa in Orlando
Luxe Sanctuary w/ Game Room & Jacuzzi | Intl Drive
10 bedrooms, 18 beds, 9 bathrooms
19–24 Sept
4.97 out of 5 average rating, 93 reviews
Top guest favourite
Townhouse in Kissimmee
Disney, Resort Style, 4 BDRM, Sleeps 8, 3 Bath
4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Kissimmee
Disney Pool Villa | Windsor Hills | Sleeps 8
3 bedrooms, 5 beds, 3 bathrooms
25–30 Oct
4.97 out of 5 average rating, 123 reviews