Rent Osceola County Homes with Swimming Pools

We selected the 235 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

Mansion Adventure

Mansion Adventure

  • 34 guests

  • 12 bedrooms

Polk County, Florida

This family-friendly mansion makes every day of your Orlando holiday feel special. Kids will love the playful themed bedrooms while grown-ups can unwind in the stylish living room or cook together in the sleek, fully equipped kitchen.

Friends, Family & Fun

Friends, Family & Fun

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

On the outskirts of Orlando, just a quick twenty-minute drive from Disney World, this spacious family home promises a stay packed with memories. Upon crossing the threshold, you’ll be hit immediately by this home’s airiness, compounded by high ceilings and a large open-plan living space.

Sunshine Residence

Sunshine Residence

  • 24 guests

  • 10 bedrooms

Polk County, Florida

This Orlando villa is well placed for family fun. And by that, we mean it's under a twenty-minute drive from Disney, plus the likes of Universal Studios and SeaWorld are nearby.

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

This brand new 5-bedroom, 4-bathroom vacation rental with a pool is located in the Storey Lake Resort, providing an unforgettable vacation. The bedrooms consist of two king bedrooms, one king suite, one bedroom with a full and twin bed, and one bedroom with a bunk bed twin over full with a twin trundle bed.


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

Explore the 235 most perfect homes in our collection

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Most popular homes in Osceola County

Castle and Cape Villa

Castle and Cape Villa

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

Lemon Blue

Lemon Blue

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Sun and Games

Sun and Games

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Disney Daydreams

Disney Daydreams

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

The Swamp Orelse

The Swamp Orelse

  • 15 guests

  • 5 bedrooms

Four Corners, Osceola County

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 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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