Holiday houses in Osceola County
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Top-rated holiday rentals in Osceola County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Osceola County holiday rentals
Other great holiday rentals in Osceola County
Guest favourite
Guest suite in Kissimmee
4.86 out of 5 average rating, 575 reviewsPrivate Studio in POOL home
Guest favourite
Cabin in Davenport
4.93 out of 5 average rating, 174 reviews$89! Cozy Cabin- Disney 20 Miles Away!
Guest favourite
Guesthouse in Kissimmee
4.97 out of 5 average rating, 32 reviewsKissimmee Studio
Guest favourite
Shipping container in Osceola County
4.94 out of 5 average rating, 49 reviewsBeautiful off-grid tiny home cottage #1
Superhost
Apartment in Kissimmee
4.8 out of 5 average rating, 200 reviews1BR w/Kitchenette near AdventHealth Orlando
Guest favourite
Apartment in Osceola County
4.8 out of 5 average rating, 41 reviewsStylish Condo, Wraparound Balcony, Disney 9 miles!
Guest favourite
Home in Kissimmee
5.0 out of 5 average rating, 75 reviewsVilla by the Lakes
Guest favourite
Home in Osceola County
5.0 out of 5 average rating, 22 reviewsCozy & Spacious Luxury Home
Destinations to explore
- Rentals with a kayak Osceola County
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- Rentals with a home theatre Osceola County
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