Book Luxury Vacation Rentals in Osceola County

Award-winning homes from £98

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Home spotlights in Osceola County

Lake Escapes

Lake Escapes

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This Orlando resort condo was made for both relaxation and excitement. Wake up to lake views from the private balcony, then dive into the fun with access to resort amenities including pools, a lazy river, golf course, gym, clubhouse, restaurant, and cinema.

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

This Orlando villa is the perfect family vacation home, with plenty of entertainment options for kids and adults alike. The themed bedrooms are a hit with the little ones, including a toy room and basketball-themed bedroom complete with over-the-top bunk beds.

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

From the private pool to the games room and movie theatre, this home sets the tone for a magical stay in Florida. There’s plenty to keep the whole group entertained with ping pong and basketball, while the themed bedrooms are a real treat for kids.

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Tailor-made for family fun, this five-bedroom home on the outskirts of Orlando is close to all the excitement of the city’s famous theme parks – but it’s just as entertaining in this sprawling house. The kids will be ecstatic with the two themed kids’ rooms – think Minions mischief and superhero adventures – and a Mario-inspired game room packed with slides, nets, hoops, Nintendo Switch, and PS4.


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

Explore the 235 most perfect homes in our collection

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Most popular homes in Osceola County

Wondrous Villa

Wondrous Villa

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Castle and Cape Villa

Castle and Cape Villa

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

 King of the Lake

King of the Lake

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Osceola County, Florida, United States. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Osceola County Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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