Book Luxury Holiday Rentals in Osceola County

Award-winning homes from £98

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Home spotlights in Osceola County

The Magic of Ketchikan

The Magic of Ketchikan

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

This luxurious vacation home has everything you need for a fun-filled family vacation. The game room features seven arcade favorites, while the gaming loft offers pool and giant scrabble competitions, karaoke, and a full bar.

Close To The Country

Close To The Country

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

This brand new vacation rental boasts 4 bedrooms and 3 bathrooms, nestled in the new phase of Champions Gate Resort. The bedrooms are comprised of a downstairs King bedroom, an upstairs master suite, and two bedrooms with a full and twin bed each.

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

This brand new vacation rental is a stunning 4-bedroom, 3-bathroom property with its own private pool. Situated in the new phase of the Champions Gate Resort, guests can enjoy the community's beautiful surrounding golf courses and tennis courts.

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This brand new vacation rental condo is located in the beautiful Storey Lake Resort and is perfect for a family or group of friends. With two bedrooms and two bathrooms, this condo comfortably accommodates up to four guests.


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

Explore the 265 most perfect homes in our collection

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Most popular homes in Osceola County

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

Grand Retreat

Grand Retreat

  • 28 guests

  • 11 bedrooms

Polk County, Florida

A Little More Sunshine

A Little More Sunshine

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Paradise on the Shore

Paradise on the Shore

  • 12 guests

  • 5 bedrooms

Osceola County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 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

Bolu-Bolu Beach

Bolu-Bolu Beach

  • 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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