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House holiday rentals in Osceola County
Find and book unique houses on Airbnb
Top-rated house rentals in Osceola County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Osceola County
House rentals with a pool
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Home in Kissimmee
4.91 out of 5 average rating, 298 reviewsFamily Home minutes from Disney!
![](https://a0.muscache.com/im/pictures/0cb99cde-7cff-4712-be8b-2326062f934b.jpg?im_w=720)
Home in Kissimmee
4.97 out of 5 average rating, 105 reviewsCozy Cove on the Lake
![](https://a0.muscache.com/im/pictures/miso/Hosting-659272327405802920/original/723506ce-f64d-462a-b82a-2d7fd6e5e70d.png?im_w=720)
Home in Kissimmee
4.88 out of 5 average rating, 117 reviewsNo Airbnb Fee! Thematic Rooms Pvt Pool °o° Area #2
![](https://a0.muscache.com/im/pictures/90759f2f-0845-4dbd-b54f-540ea70acd88.jpg?im_w=720)
Home in Kissimmee
4.9 out of 5 average rating, 118 reviewsPrivate pool home close to Disney
![](https://a0.muscache.com/im/pictures/miso/Hosting-30309715/original/584d1812-21b9-434c-b3df-4c28b07d9f54.jpeg?im_w=720)
Home in Kissimmee
4.9 out of 5 average rating, 102 reviewsCountry Creek Villas LLC
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Home in Kissimmee
5 out of 5 average rating, 177 reviewsWindsor Orlando Private Arcades,Theater,Pool-Spa
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Home in Kissimmee
5 out of 5 average rating, 3 reviewsCarpe-D Lake Marion Resort Vacation Villa
![](https://a0.muscache.com/im/pictures/miso/Hosting-797882744138152833/original/ddefd560-eb46-4260-9cbf-81807aa83f7d.jpeg?im_w=720)
Home in Osceola County
5 out of 5 average rating, 22 reviewsCozy & Spacious Luxury Home
Weekly house rentals
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Home in Lake Wales
4.9 out of 5 average rating, 80 reviews"Cutty Shack" Waterfront Kissimmee River House 3/3
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Home in Lake Wales
4.94 out of 5 average rating, 17 reviewsCozy House near to Legoland FL
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Home in Lake Wales
4.95 out of 5 average rating, 21 reviewsLake Rosalie Getaway
![](https://a0.muscache.com/im/pictures/miso/Hosting-12535221/original/0ec18eb6-d556-408a-8a37-2123e832d617.jpeg?im_w=720)
Home in Lake Wales
4.92 out of 5 average rating, 91 reviewsLake house 3/2 Fish 4 Monster Bass! Kayak & Canoe
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Home in Kissimmee
4.96 out of 5 average rating, 27 reviewsCheerful, 3 bedroom home with pool
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Home in Lake Wales
4.92 out of 5 average rating, 77 reviews*This must be THE PLACE FL*
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Home in Frostproof
4.9 out of 5 average rating, 10 reviewsLake Reedy Living Winter Season 24-25 Now Avail.
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Home in Kissimmee
4.79 out of 5 average rating, 48 reviewsNewly Renovated Kissimmee Duplex
Private house rentals
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Home in Lake Wales
5 out of 5 average rating, 22 reviewsCabin on Lake Walk In Water
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Home in Kissimmee
5 out of 5 average rating, 38 reviewsDream Vacation w/Avengers, Star Wars, & Mario Kart
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Home in Winter Haven
4.9 out of 5 average rating, 59 reviews3-br peaceful home near Legoland
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Home in Kissimmee
4.96 out of 5 average rating, 25 reviewsEntire home near theme parks, restaurants & more!
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Home in Kissimmee
4.96 out of 5 average rating, 74 reviewsVacation Home 3 bedroom/2 full bath/private pool
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Home in St. Cloud
4.95 out of 5 average rating, 19 reviewsLakeshore Home w/Private Pool.
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Home in Kissimmee
5 out of 5 average rating, 45 reviewsAmazing apartment kissimmee Excellent location
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Home in Osceola County
4.92 out of 5 average rating, 24 reviewsLarge Private Home on Golf course by Disney
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