Rent Osceola County Homes with Swimming Pools

We selected the 233 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Osceola County

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

If you're planning an action-packed trip to Florida and want to be close to the good stuff, this family home may do the trick. It's set in a resort – the closest to Walt Disney World – and well-positioned to make the most of the nearby shopping malls and top attractions.

Way Home

Way Home

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Fun and joy come to life in this Florida home. From the themed bedrooms and the games room to the private pool and spa, this is the perfect spot for a magical family getaway.

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Perfectly positioned in the sought-after Storey Lake Resort, this brand-new four-bedroom home brings comfort and convenience to an unforgettable Orlando getaway. With a private pool and bright, modern interiors, it’s ideal for families and groups visiting nearby Disney World.

Sunshine, Always

Sunshine, Always

  • 6 guests

  • 3 bedrooms

Osceola County, Florida

This brand new vacation rental condo in Storey Lake Resort is a stunning 3-bedroom, 2-bathroom property that promises guests an unforgettable stay. The condo includes one queen bedroom en suite and two additional bedrooms with queen beds each.


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

Explore the 233 most perfect homes in our collection

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Most popular homes in Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Casa Rosita

Casa Rosita

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Orange Vista

Orange Vista

  • 18 guests

  • 6 bedrooms

Polk County, Florida

 King of the Lake

King of the Lake

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

The Blue Dunes

The Blue Dunes

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Castle and Cape Villa

Castle and Cape Villa

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

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Check upcoming rates & availability for Osceola County Homes with Swimming Pools


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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