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We selected the 235 luxury monthly villas and homes worth renting in this location

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Home spotlights in Osceola County

For You Love

For You Love

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Nestled in a private resort, this home is perfectly placed for a fun-filled adventure in Florida. It’s just a short drive to Walt Disney World and the main attractions in Kissimmee – including walking paths, playgrounds and restaurants.

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Perfectly positioned in the sought-after Storey Lake Resort, this brand-new four-bedroom home brings comfort and convenience to an unforgettable Orlando getaway. With a private pool and bright, modern interiors, it’s ideal for families and groups visiting nearby Disney World.

The Entertainment Enclave

The Entertainment Enclave

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Welcome to a haven of fun for the whole family. Home entertainment of every type is available here, for both children and adults – kids will love the dedicated arcade room, themed bedrooms including integrated bunk beds, and a video games room complete with karaoke.

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 235 most perfect homes in our collection

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Most popular homes in Osceola County

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

The Last Frontier

The Last Frontier

  • 11 guests

  • 4 bedrooms

Four Corners, Osceola County

Moon Over Lake

Moon Over Lake

  • 34 guests

  • 12 bedrooms

Polk County, Florida

The Blue Ledge

The Blue Ledge

  • 18 guests

  • 6 bedrooms

Polk County, Florida

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Wondrous Villa

Wondrous Villa

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

 King of the Lake

King of the Lake

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

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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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