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Search results; Over 1,000 homes in Kissimmee

Top guest favorite
Condo in Kissimmee
Luxury 3 Bed/2 Bath Condo 4 miles from WDW
3 bedrooms, 4 beds, 2 private baths
Aug 15 – 20
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4.88 out of 5 average rating, 130 reviews
Villa in Kissimmee
Spacious villa w/pool & spa & game room
5 bedrooms, 7 beds, 5 baths
Dec 27 – Jan 1
5.0 out of 5 average rating, 4 reviews
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 baths
Aug 31 – Sep 5
New place to stay
Superhost
Home in Kissimmee
9BR Pixar Theater Game Room | Pool Spa | Sleeps 27
9 bedrooms, 19 beds, 5 baths
Aug 12 – 17
New place to stay
Top guest favorite
Townhouse in Kissimmee
Disney Theme Rooms | Private Pool | Storey Lake
4 bedrooms, 6 beds, 3 baths
Nov 2 – 7
5.0 out of 5 average rating, 39 reviews
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds, 5 baths
Aug 16 – 21
New place to stay
Guest favorite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 baths
Aug 22 – 27
5.0 out of 5 average rating, 12 reviews
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 baths
Aug 24 – 29
New place to stay
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds, 4 baths
Oct 24 – 29
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Kissimmee
2026 NEW 06 Bedrooms at Solara Resort/Private Pool
6 bedrooms, 9 beds, 4.5 baths
Oct 4 – 9
5.0 out of 5 average rating, 16 reviews
Top guest favorite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 baths
Aug 16 – 21
5.0 out of 5 average rating, 16 reviews
Home in Kissimmee
Golden Haven | 5BR | Pool | 12 Min to Disney
5 bedrooms, 7 beds, 4.5 baths
Aug 16 – 21
5.0 out of 5 average rating, 4 reviews
Villa in Kissimmee
Cumbrian Dream 4 Bedroom Pool Home near Disney
4 bedrooms, 6 beds, 3 baths
Aug 25 – 30
Top guest favorite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 baths
Sep 28 – Oct 3
4.98 out of 5 average rating, 40 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 baths
Oct 2 – 7
New place to stay
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds, 4 baths
Oct 5 – 10
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds, 2.5 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Davenport
A Magical Villa at Watersong
5 bedrooms, 7 beds, 4 baths
Aug 23 – 28
5.0 out of 5 average rating, 4 reviews