Rent Osceola County Homes with Swimming Pools

We selected the 277 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

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This brand new 2 bedroom, 2 bathroom vacation rental condo is located in Storey Lake Resort, making it the perfect spot for an unforgettable vacation. The condo features a king bedroom on suite, as well as a bedroom with a full bed, twin bed, and sofa bed.

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

This is a luxurious vacation home located in a resort area. With 71 luxury homes and exclusive amenities, this brand new one-of-a-kind vacation community offers a private entrance, scenic views, and a covered playground.

Sunshine Beach

Sunshine Beach

  • 28 guests

  • 11 bedrooms

Polk County, Florida

This is a mid-century modern home that is chic and understated in design. The high-end kitchen features premium appliances, elegant blue and cream cabinetry, and stone countertops.

The Magic of Disney

The Magic of Disney

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

This vacation home in The resort is perfect for families with kids who will love the Winter and Superhero-themed bedrooms, private home theater, game room/loft, and private screened-in pool and spa. The game room has a karaoke system, mini jungle gym, arcade games, and a lounge area with a smart TV.


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

Explore the 277 most perfect homes in our collection

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Most popular homes in Osceola County

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

Just Another Day At The Beach

Just Another Day At The Beach

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Paradise on the Shore

Paradise on the Shore

  • 12 guests

  • 5 bedrooms

Osceola County, Florida

The Blue Forger

The Blue Forger

  • 28 guests

  • 10 bedrooms

Polk County, Florida

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

The Blue Burdock

The Blue Burdock

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

A History of the Sun

A History of the Sun

  • 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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