Book Luxury Holiday Rentals in Osceola County

Award-winning homes from £98

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Home spotlights in Osceola County

The Tallest Tree

The Tallest Tree

  • 28 guests

  • 10 bedrooms

Polk County, Florida

This is a luxurious and spacious 11-bedroom vacation home that offers a wide range of amenities for guests of all ages. The grand entrance welcomes visitors into an upscale central living area with sleek couches and modern furnishings.

Grand Retreat

Grand Retreat

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Entrance/Great Room: The sumptuous experience begins as guests step into the grand foyer of this 7,200-square-foot retreat. From there, they continue to the great room—a luxurious, centralized living area that exudes the allure of a beautiful hotel lobby.

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.

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

One thing’s for sure in this Floridian home – you’ll never be bored. Jam-packed with entertainment options including a home cinema, games room, private pool and hot tub, there’s something for everyone here.


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

Explore the 305 most perfect homes in our collection

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Most popular homes in Osceola County

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

The Mud House

The Mud House

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Sailing On A Sunshine Day

Sailing On A Sunshine Day

  • 18 guests

  • 6 bedrooms

Polk County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

The Pineapple Gate

The Pineapple Gate

  • 24 guests

  • 9 bedrooms

Polk County, Florida

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

The Blue Burdock

The Blue Burdock

  • 24 guests

  • 9 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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