Book Luxury Short Stay Rentals in Osceola County

We selected the 314 homes worth renting in this location

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Home spotlights in Osceola County

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This brand new vacation rental condo is located in the beautiful Storey Lake Resort and is perfect for a family or group of friends. With two bedrooms and two bathrooms, this condo comfortably accommodates up to four guests.

Under the Sea Escape

Under the Sea Escape

  • 12 guests

  • 6 bedrooms

Polk County, Florida

If you're looking for a family-friendly vacation rental near Disney World, look no further than this stunning home in the Solterra Resort. With its pirate-themed bunk room, Star Wars arcade, and sports-themed den, this home has something for everyone.

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.

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.


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

Explore the 314 most perfect homes in our collection

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Most popular homes in Osceola County

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

The Tallest Tree

The Tallest Tree

  • 28 guests

  • 10 bedrooms

Polk County, Florida

Magical Disney Haven

Magical Disney Haven

  • 25 guests

  • 9 bedrooms

Four Corners, Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Kid's Dream Villa

Kid's Dream Villa

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

The Scholar's Shanty

The Scholar's Shanty

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola 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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