Book Luxury Holiday Rentals in Osceola County

Award-winning homes from £98

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Osceola County

The Time Traveler's Daughter

The Time Traveler's Daughter

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

This vacation home is perfect for families looking to have a fun-filled retreat. The kids will love the jungle-themed bedroom with tree trunk bunk beds and the toy-themed bedroom with floor-to-ceiling wall art of their favorite toys.

A Little Piece of Sunshine

A Little Piece of Sunshine

  • 28 guests

  • 11 bedrooms

Polk County, Florida

This villa is a luxurious and spacious 7,200-square-foot mansion in Orlando, Florida. This stunning property boasts a chef's kitchen with black marble countertops and upgraded appliances, an adjacent versatile dining room, and a beautiful great room with modern couches and chairs.

The Blue Otter's Nest

The Blue Otter's Nest

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

This brand new single-family home in Champions Gate boasts luxury and comfort with six bedrooms and five bathrooms, one of which is located downstairs. The fully equipped kitchen and laundry room make it easy to feel at home.

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

View on map

Most popular homes in Osceola County

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Palm Trees & Paintbrush

Palm Trees & Paintbrush

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

Hurricanes in Summer

Hurricanes in Summer

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

View all

Check upcoming rates & availability for Osceola County Holiday Rentals


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.

Search Our Collection