Book Luxury Holiday Rentals in Osceola County

Award-winning homes from £98

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Home spotlights in Osceola County

A Disney Mania

A Disney Mania

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

This 6-bed/5-bath villa in Orlando is perfect for a family vacation. The villa features two epic-themed bedrooms, including a Minions and Ironman bedroom, that will keep the kids entertained all night long.

Sunshine on the Seaside

Sunshine on the Seaside

  • 11 guests

  • 4 bedrooms

Campbell, Osceola County

This stunning brand new vacation rental features four bedrooms and three bathrooms, including a king bedroom downstairs, a king suite, a full/twin bed bedroom, and a bunk bed with a twin over full and trundle twin bed. Located in the popular Storey Lake Resort, guests will enjoy easy access to Disney, Disney Springs, malls, and Walmart.

A History of the Sun

A History of the Sun

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This brand new vacation rental in Storey Lake Resort boasts 4 bedrooms and 3 bathrooms, including a king bedroom downstairs and a king suite. It also features a bedroom with a full and twin bed, as well as a bedroom with a bunk bed twin over full.

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

This is the perfect vacation home for families looking for a fun-filled getaway. Kids will love the superhero and Fashionista-themed bedrooms, complete with over-the-top bunk beds and decor.


We selected the top 3% holiday homes in Osceola County Holiday Rentals

Explore the 277 most perfect homes in our collection

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Most popular homes in Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Just Another Day At The Beach

Just Another Day At The Beach

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

The Magic of Osceola

The Magic of Osceola

  • 17 guests

  • 4 bedrooms

Four Corners, Osceola County

The Blue Forger

The Blue Forger

  • 28 guests

  • 10 bedrooms

Polk County, Florida

Sunshine Beach

Sunshine Beach

  • 28 guests

  • 11 bedrooms

Polk County, Florida

The Blue Burdock

The Blue Burdock

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Lemon Blue

Lemon Blue

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Osceola County, Florida, United States. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Osceola County, Florida, United States has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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