Book Luxury Short Stay Rentals in Osceola County

We selected the 235 homes worth renting in this location

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Home spotlights in Osceola County

The Magic of Osceola

The Magic of Osceola

  • 17 guests

  • 4 bedrooms

Four Corners, Osceola County

This luxurious single-family home boasts six bedrooms and six bathrooms, including one suite on the first floor and two on the second floor. The property features a fully equipped kitchen, private screened pool and spa, game room with pool and ping pong tables, and a spacious loft upstairs.

A Tale of Magic

A Tale of Magic

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Just a short drive from Disney, this home places you in a magical part of Florida. Days can be spent exploring the local attraction parks or Downtown Orlando and Kissimmee.

Orange Vista

Orange Vista

  • 18 guests

  • 6 bedrooms

Polk County, Florida

It's all about location with this villa, set in a family-friendly resort. Not only is it less than twenty-five minutes in the car to Disney, but it's also a great base for exploring Universal Studios, SeaWorld and other local attractions.

Castle and Cape Villa

Castle and Cape Villa

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

Looking for the ultimate group getaway in Florida? This spacious villa in Kissimmee is where family fun meets luxury living.


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

Explore the 235 most perfect homes in our collection

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Most popular homes in Osceola County

Wonder Mansion

Wonder Mansion

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Citrus Garden Breeze

Citrus Garden Breeze

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

Sunshine Beach

Sunshine Beach

  • 28 guests

  • 11 bedrooms

Polk County, Florida

A True Joy

A True Joy

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Moon Over Lake

Moon Over Lake

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Friends, Family & Fun

Friends, Family & Fun

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

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Check upcoming rates & availability for Osceola County Short Stay Rentals


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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