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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Cottage in Kissimmee
2BD Cottage in Margaritaville w Playground in back
2 bedrooms, 2 beds, 2.5 private bathrooms
2–7 Aug
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4.96 out of 5 average rating, 69 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
7–12 Dec
New place to stay
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
9 bedrooms, 12 beds
1–6 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds
21–26 Aug
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Kissimmee
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds
30 Jul – 4 Aug
Superhost
Home in Kissimmee
Amazing 6-bedroom home with private spa
6 bedrooms, 6 beds
20–25 Aug
New place to stay
Superhost
Townhouse in Davenport
5 Bedroom Luxe Disney Villa with Pool & Water Park
5 bedrooms, 10 beds
2–7 Aug
New place to stay
Home in Kissimmee
Magical Villa with Themed Bedrooms at Reunion
6 bedrooms, 10 beds
27 Jul – 1 Aug
New place to stay
Home in Kissimmee
Poolside Heaven in Cumbrian Lakes
4 bedrooms, 6 beds
13–18 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms, 4 beds
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds
1–6 Aug
Superhost
Home in Kissimmee
13-Min Disney | Priv Pool | 5BR Storey Lake Resort
5 bedrooms, 4 beds
2–7 Aug
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds
1–6 Aug
New place to stay
Home in Kissimmee
5BR Fantastic Villa Pool & Game Room Near Disney
5 bedrooms, 7 beds
11–16 Aug
New place to stay
Superhost
Home in Orlando
Themed 5BR Villa Minutes from Disney & Universal
5 bedrooms, 7 beds
1–6 Sept
Superhost
Home in Kissimmee
7 BD/ 7 BA/ Solara Resort (2327 SR)
7 bedrooms, 10 beds
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Kissimmee
Pvt Pool&Spa·Game Room·BBQ·Near Theme Parks
5 bedrooms, 9 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Kissimmee
5 BD/ 5 BA/ Reunion Village (7852 MP)
5 bedrooms, 7 beds
24–29 Jul