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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Home in Kissimmee
Game Room/HeatedPool/Piano Upscale Waterfront Home
3 bedrooms, 4 beds, 2 private bathrooms
14–19 Sept
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4.97 out of 5 average rating, 358 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
Superhost
Apartment in Kissimmee
304_Mickey's Slide & Chef Remy Escape
2 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Kissimmee
Luxury Reunion Retreat Patio Views Near Disney
5 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
New place to stay
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
Superhost
Home in Kissimmee
Luxury NEW 09 Bedroom/Pool At Solara Resort
9 bedrooms, 9 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
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
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
9BR Pixar Theater Game Room | Pool Spa | Sleeps 27
9 bedrooms, 19 beds, 5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Davenport
Private Pool & Spa | Single-Story 4BR | Disney |
4 bedrooms, 4 beds, 3 bathrooms
31 Oct – 5 Nov
New place to stay
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
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
Guest favourite
Home in Davenport
A Magical Villa at Watersong
5 bedrooms, 7 beds, 4 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Townhouse in Kissimmee
5BR to Gather, Relax and Make Memories (2640ST)
5 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
5.0 out of 5 average rating, 38 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, 5 reviews
Guest favourite
Home in Davenport
Star Wars & Wizard Themed XL Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Rooms in Kissimmee
4164 Themed 5BR Near Disney w/ Pool
5 bedrooms, 8 beds, 4 bathrooms
14–19 Sept
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, 13 reviews
Superhost
Home in Clermont
2026 NEW Themed 5-Bedroom Home at Windsor Cay
5 bedrooms, 5 beds, 4 bathrooms
29 Nov – 4 Dec