Rent Osceola County Homes with Swimming Pools

We selected the 281 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

Grand Retreat

Grand Retreat

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Entrance/Great Room: The sumptuous experience begins as guests step into the grand foyer of this 7,200-square-foot retreat. From there, they continue to the great room—a luxurious, centralized living area that exudes the allure of a beautiful hotel lobby.

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.

The Magic of Ketchikan

The Magic of Ketchikan

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

This luxurious vacation home has everything you need for a fun-filled family vacation. The game room features seven arcade favorites, while the gaming loft offers pool and giant scrabble competitions, karaoke, and a full bar.

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

This brand new vacation rental is a stunning 4-bedroom, 3-bathroom property with its own private pool. Situated in the new phase of the Champions Gate Resort, guests can enjoy the community's beautiful surrounding golf courses and tennis courts.


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

Explore the 281 most perfect homes in our collection

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Most popular homes in Osceola County

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

The Time Traveler's Daughter

The Time Traveler's Daughter

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

The Sun & White

The Sun & White

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

The Great Florida

The Great Florida

  • 16 guests

  • 7 bedrooms

Four Corners, Osceola County

Fisk Bayview

Fisk Bayview

  • 28 guests

  • 10 bedrooms

Polk County, Florida

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Lemon Blue

Lemon Blue

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Pines & Greenwood

Pines & Greenwood

  • 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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