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Search results; Over 1,000 homes in Kissimmee

Superhost
Tiny home in Kissimmee
Luxury Tiny Cottage. Only 5 miles from Disney!
1 bedroom, 2 beds, 1 private bathroom
18–23 Sept
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4.86 out of 5 average rating, 180 reviews
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
Townhouse in Kissimmee
NEW Beautiful Townhome Near Disney w/ Themed Room
3 bedrooms, 6 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 27 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
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
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
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
5BR to Gather, Relax and Make Memories (2640ST)
5 bedrooms, 6 beds, 4 bathrooms
11–16 Oct
5.0 out of 5 average rating, 38 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
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
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
Luxury NEW 09 Bedroom/Pool At Solara Resort
9 bedrooms, 9 beds, 6.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
4BR house with private pool in Magic Village
4 bedrooms, 6 beds, 4.5 bathrooms
13–18 Sept
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
Superhost
Home in Kissimmee
12BR Luxury Disney Villa/Sleeps 29/Arcade/Pool
12 bedrooms, 22 beds, 11.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Kissimmee
Luxury Reunion Retreat Patio Views Near Disney
5 bedrooms, 6 beds, 4 bathrooms
13–18 Sept
New place to stay
Home in Kissimmee
Superhero HQ: Private Pool & Spa Near Disney
5 bedrooms, 6 beds, 4.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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
Superhost
Home in Kissimmee
NEW Home Luxury 04 Bedrooms At Storey Lake
4 bedrooms, 6 beds, 3 bathrooms
14–19 Dec