Book Luxury Vacation Rentals with a Private Chef in Osceola County

We selected the 235 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Osceola County

Disney Daydreams

Disney Daydreams

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

Just twenty minutes from Disney World, this villa makes family holidays feel like a breeze. Inside, there’s room for everyone to spread out, with a second living room upstairs and a private games room to keep the kids entertained.

The Swamp Orelse

The Swamp Orelse

  • 15 guests

  • 5 bedrooms

Four Corners, Osceola County

This brand new single-family home is located in Champions Gate and boasts 5 bedrooms and 5 bathrooms, with 2 bedrooms located downstairs. The fully equipped kitchen leads to a screened-in private pool and spa, perfect for relaxing after a long day at Disney or shopping at nearby centers.

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

This brand new penthouse vacation rental is located in the Storey Lake Resort, just a stone's throw away from Disney, Disney Springs, Malls and Walmart. With four bedrooms and three bathrooms, this property is perfect for families or groups of up to 12 guests.

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 Vacation Rentals with a Private Chef

Explore the 235 most perfect homes in our collection

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Most popular homes in Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Citrus Garden Breeze

Citrus Garden Breeze

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

Strawberry Sunrise

Strawberry Sunrise

  • 18 guests

  • 6 bedrooms

Polk County, Florida

The Magic of Osceola

The Magic of Osceola

  • 17 guests

  • 4 bedrooms

Four Corners, Osceola County

For You Love

For You Love

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

 King of the Lake

King of the Lake

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

Palmview Paradise

Palmview Paradise

  • 5 guests

  • 2 bedrooms

Osceola County, Florida

Orlando Adventure

Orlando Adventure

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

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Frequently asked questions

Explore our unbeatable collection of luxury Vacation Rentals with a Personal Chef in Osceola County, Florida, United States. Each and every home in our range comes fully furnished with excellently-equipped kitchens, essential bathroom toiletries, and all necessary linens included. Tested aspects of any home range from Wifi speed and shower pressure to a space's feel and design, so there really is nothing left to chance on our mission to discover the greatest properties on offer. Enjoy a stay in one of the Holiday Rentals in Osceola County with a Private Chef today, and remember your trip for all the right reasons. And don't hesitate to contact our team of experts if you require any assistance, as it is their pleasure to help make the process easy.

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