Rent Osceola County Homes with Swimming Pools

We selected the 337 homes worth renting in this location

Home spotlights in Osceola County

The Shores of the Swayed House

The Shores of the Swayed House

  • 17 guests

  • 6 bedrooms

Osceola County, Florida

This brand new single-family home boasts six bedrooms and five bathrooms, as well as a game room in the garage. One bedroom is conveniently located downstairs, and the fully equipped kitchen provides everything needed for a comfortable stay.

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.

The Reapers

The Reapers

  • 10 guests

  • 5 bedrooms

Four Corners, Osceola County

This stunning vacation rental is a brand new 5 bedroom, 4 bathroom property that boasts a beautiful pool and water view. The property is located in the sought-after Champions Gate Resort and features two downstairs bedrooms, one with a queen bed and the other with two twin beds, while upstairs there are two king bedrooms and another bedroom with two twin beds.

The Time Traveler's Daughter

The Time Traveler's Daughter

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

This vacation home is perfect for families looking to have a fun-filled retreat. The kids will love the jungle-themed bedroom with tree trunk bunk beds and the toy-themed bedroom with floor-to-ceiling wall art of their favorite toys.


We selected the top 3% holiday homes in Osceola County Homes with Swimming Pools

Explore the 337 most perfect homes in our collection

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Most popular homes in Osceola County

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

Under the Sea Escape

Under the Sea Escape

  • 12 guests

  • 6 bedrooms

Polk County, Florida

Sarasota Hotel

Sarasota Hotel

  • 5 guests

  • 2 bedrooms

Osceola County, Florida

On the Ocean

On the Ocean

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Ocean's Voice

The Ocean's Voice

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Kid's Dream Villa

Kid's Dream Villa

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

A Thousand Sunny Days

A Thousand Sunny Days

  • 10 guests

  • 3 bedrooms

Four Corners, Osceola County

Sunshine Haze

Sunshine Haze

  • 20 guests

  • 7 bedrooms

Kissimmee, Osceola County

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Popular in Osceola County

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Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Osceola County, Florida, United States. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Osceola County Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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