Book Luxury Short Stay Rentals in Osceola County

We selected the 290 homes worth renting in this location

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Age 13+

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Children

Age 1 to 12

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Home spotlights in Osceola County

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

This stunning vacation home, located in a resort community, is perfect for families looking for a magical and luxurious getaway. The house features two themed bedrooms - one with life-sized wizards and the other with Hawaiian beach decor - that are sure to delight kids.

A History of the Sun

A History of the Sun

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This brand new vacation rental in Storey Lake Resort boasts 4 bedrooms and 3 bathrooms, including a king bedroom downstairs and a king suite. It also features a bedroom with a full and twin bed, as well as a bedroom with a bunk bed twin over full.

The Magic of Disney

The Magic of Disney

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

This vacation home in The resort is perfect for families with kids who will love the Winter and Superhero-themed bedrooms, private home theater, game room/loft, and private screened-in pool and spa. The game room has a karaoke system, mini jungle gym, arcade games, and a lounge area with a smart TV.

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.


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

Explore the 290 most perfect homes in our collection

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Most popular homes in Osceola County

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Sunshine on the Seaside

Sunshine on the Seaside

  • 11 guests

  • 4 bedrooms

Campbell, Osceola County

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

The Sunshine of Your Eyes

The Sunshine of Your Eyes

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Sargasso Seas

Sargasso Seas

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

Grand Retreat

Grand Retreat

  • 28 guests

  • 11 bedrooms

Polk County, Florida

The Oceanaire

The Oceanaire

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

Fisk Bayview

Fisk Bayview

  • 28 guests

  • 10 bedrooms

Polk County, Florida

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Osceola County, Florida, United States. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Osceola County luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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