Rent Osceola County Homes with Swimming Pools

We selected the 346 homes worth renting in this location

Home spotlights in Osceola County

Body of Evidence

Body of Evidence

  • 15 guests

  • 4 bedrooms

Kissimmee, Osceola County

This beautiful brand new single-family home in the Storey Lake community is equipped with five bedrooms and five bathrooms, with two bedrooms conveniently located downstairs. The kitchen is fully equipped and the house also features a screened private pool and spa, as well as a game room for entertainment.

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.

A Little Hike

A Little Hike

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This brand new 2-bedroom, 2-bathroom vacation rental condo is located in the beautiful Storey Lake Resort and promises guests an amazing stay. The condo features a king bedroom with an en-suite bathroom and another bedroom with a queen bed.

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This stunning brand new vacation rental is a 4 bedroom, 3 bathroom property located in Storey Lake Resort. With two king bedrooms, one queen bedroom, and a bedroom with 2 twin beds plus a full sofa bed, this property can comfortably accommodate up to 10 guests.


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

Explore the 346 most perfect homes in our collection

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Most popular homes in Osceola County

On the Ocean

On the Ocean

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Sea Dragon

The Sea Dragon

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Celine Dion

Celine Dion

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Gatorland

Gatorland

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

The Flamingo Vista

The Flamingo Vista

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Sugar Maple

The Sugar Maple

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Coral Reefs In The Sun

Coral Reefs In The Sun

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

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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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