Rent Osceola County Homes with Swimming Pools

We selected the 236 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Osceola County

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

This home sets the stage for magical stay in Florida. It’s just a short drive to Disney World, Disney Springs as well as the centre of Kissimmee where you’ll find all the amenities you could need.

The Blue Ledge

The Blue Ledge

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Welcome to this home, a stunning 4,000-square-foot Transitional-style villa located in a resort community. This luxury vacation home features seven bedrooms, including a jaw-dropping arctic-themed kids' room that sleeps six and a spacious master bedroom with an en suite bath, walk-in closet, double sinks, shower, and bathtub.

Game On Villa

Game On Villa

  • 24 guests

  • 6 bedrooms

Polk County, Florida

Just over a twenty-minute drive from Disney, this Orlando villa is perfectly placed for family fun, with Universal Studios, SeaWorld and more also close by. The LEGO and space-themed bedrooms with custom bunk beds will keep little ones happy.

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

This family home offers plenty of space and style for your dream Florida getaway. The kitchen is fully equipped, perfect for whipping up meals to enjoy outside by the screened private pool and spa.


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

Explore the 236 most perfect homes in our collection

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Most popular homes in Osceola County

Wondrous Villa

Wondrous Villa

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

A Little Piece of Sunshine

A Little Piece of Sunshine

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Wonder Mansion

Wonder Mansion

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Way Home

Way Home

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

A Tale of Magic

A Tale of Magic

  • 28 guests

  • 11 bedrooms

Polk County, Florida

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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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