Rent Osceola County Homes with Swimming Pools

We selected the 314 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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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

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.

Under the Sea Escape

Under the Sea Escape

  • 12 guests

  • 6 bedrooms

Polk County, Florida

If you're looking for a family-friendly vacation rental near Disney World, look no further than this stunning home in the Solterra Resort. With its pirate-themed bunk room, Star Wars arcade, and sports-themed den, this home has something for everyone.

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

This is the perfect vacation home for families looking for a fun-filled getaway. Kids will love the superhero and Fashionista-themed bedrooms, complete with over-the-top bunk beds and decor.

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.


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

Explore the 314 most perfect homes in our collection

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Most popular homes in Osceola County

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

The Tallest Tree

The Tallest Tree

  • 28 guests

  • 10 bedrooms

Polk County, Florida

Magical Disney Haven

Magical Disney Haven

  • 25 guests

  • 9 bedrooms

Four Corners, Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Kid's Dream Villa

Kid's Dream Villa

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

The Scholar's Shanty

The Scholar's Shanty

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 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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