Rent Osceola County Homes with Swimming Pools

We selected the 261 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

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

This luxurious new single-family home boasts six bedrooms, six bathrooms, and a game room complete with air hockey, pool table, and ping pong. The first floor features one suite while the second floor has two suites and a spacious loft.

So Much Better

So Much Better

  • 34 guests

  • 12 bedrooms

Polk County, Florida

This is a luxurious villa located within a resort. The villa boasts world-class elegance with its Transitional decor and top-quality appliances in the fully equipped kitchen.

Taller Than Life

Taller Than Life

  • 13 guests

  • 4 bedrooms

Osceola County, Florida

This brand new single-family home is perfect for those looking for a luxurious stay in the heart of Orlando. The cozy house features five bedrooms and five bathrooms, with two bedrooms conveniently located on the ground floor.

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 261 most perfect homes in our collection

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Most popular homes in Osceola County

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

The Alabaster Air

The Alabaster Air

  • 28 guests

  • 10 bedrooms

Polk County, Florida

The Indian Village

The Indian Village

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Tallest Tree

The Tallest Tree

  • 28 guests

  • 10 bedrooms

Polk County, Florida

Bolu-Bolu Beach

Bolu-Bolu Beach

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

All The Lights That You Cannot See

All The Lights That You Cannot See

  • 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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