Book Luxury Vacation Rentals with a Private Chef in Osceola County

We selected the 266 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Osceola County

Taller Than Life

Taller Than Life

  • 13 guests

  • 4 bedrooms

Osceola County, Florida

This brand new single-family home is perfect for those looking for a luxurious stay in the heart of Orlando. The cozy house features five bedrooms and five bathrooms, with two bedrooms conveniently located on the ground floor.

The Pineapple Gate

The Pineapple Gate

  • 24 guests

  • 9 bedrooms

Polk County, Florida

This villa is a perfect vacation destination for families with children, featuring themed bedrooms that include the ocean princess and Galactica rooms. Children will also love the arcade, game loft, and home theater.

The Blue Ocean

The Blue Ocean

  • 7 guests

  • 2 bedrooms

Kissimmee, Osceola County

This brand new 2 bedroom, 2 bathroom vacation rental condo is located in the beautiful Storey Lake Resort, providing guests with an amazing vacation experience. The condo boasts a king bedroom with an en-suite bathroom, as well as another bedroom featuring a full bed, twin bed and sofa bed.

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This brand new 2 bedroom, 2 bathroom vacation rental condo is located in Storey Lake Resort, making it the perfect spot for an unforgettable vacation. The condo features a king bedroom on suite, as well as a bedroom with a full bed, twin bed, and sofa bed.


We selected the top 3% holiday homes in Osceola County Vacation Rentals with a Private Chef

Explore the 266 most perfect homes in our collection

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Most popular homes in Osceola County

The Magic of Osceola

The Magic of Osceola

  • 17 guests

  • 4 bedrooms

Four Corners, Osceola County

Gator's Daughter

Gator's Daughter

  • 34 guests

  • 11 bedrooms

Polk County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Bonsai & Blue Sky

Bonsai & Blue Sky

  • 34 guests

  • 12 bedrooms

Polk County, Florida

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

The Magic of Disney

The Magic of Disney

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Strawberry Bikini

Strawberry Bikini

  • 18 guests

  • 6 bedrooms

Polk County, Florida

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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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