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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Home in Kissimmee
Reunion Resort pool home with hot tub - 4 bedrooms
4 bedrooms, 5 beds, 3.5 private bathrooms
23–28 Jul
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4.95 out of 5 average rating, 74 reviews
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5.0 out of 5 average rating, 15 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
21–26 Aug
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
New place to stay, 9 bedrooms, 12 beds, 6 bathrooms
1–6 Aug
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
7–12 Dec
Superhost
Home in Kissimmee
Amazing 6-bedroom home with private spa
New place to stay, 6 bedrooms, 6 beds, 5.5 bathrooms
20–25 Aug
Superhost
Home in Kissimmee
13-Min Disney | Priv Pool | 5BR Storey Lake Resort
5 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Superhost
Home in Orlando
Themed 5BR Villa Minutes from Disney & Universal
5 bedrooms, 7 beds, 5 bathrooms
1–6 Sept
Home in Kissimmee
Magical Villa with Themed Bedrooms at Reunion
New place to stay, 6 bedrooms, 10 beds, 5 bathrooms
27 Jul – 1 Aug
Home in Kissimmee
Lakefront Charmer 8BR 6BA Home Cinema Pool/Spa
New place to stay, 8 bedrooms, 13 beds, 6 bathrooms
26–31 Jul
Superhost
Townhouse in Davenport
5 Bedroom Luxe Disney Villa with Pool & Water Park
New place to stay, 5 bedrooms, 10 beds, 4.5 bathrooms
2–7 Aug
Guest favourite
Home in Kissimmee
Pvt Pool&Spa·Game Room·BBQ·Near Theme Parks
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
28 Aug – 2 Sept
Guest favourite
Home in Kissimmee
Brand New 07 Bedrooms At Solara Resort
5.0 out of 5 average rating, 23 reviews, 7 bedrooms, 10 beds, 5 bathrooms
9–14 Aug
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
Superhost
Apartment in Kissimmee
Perfect 2BD Family Condo w/ Balcony Near Disney
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
New place to stay, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
1–6 Aug
Superhost
Home in Kissimmee
5 BD/ 5 BA/ Reunion Village (7852 MP)
5 bedrooms, 7 beds, 5 bathrooms
24–29 Jul
Superhost
Flat in Kissimmee
Sleeps 10*Private Pool*Clubhouse Amenities
New place to stay, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul