Rent Osceola County Homes with Swimming Pools

We selected the 232 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

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.

Citrus Garden Breeze

Citrus Garden Breeze

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

Wake up in your Orlando hideaway and decide what the day will bring: a family adventure at Disney, just minutes away, or a lazy morning floating down a winding river under the Florida sun. Return to the perfect spot for a coffee or an evening wine, the the balcony overlooking the garden.

Lemon Blue

Lemon Blue

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

This house boasts an impressive array of themed rooms and entertainment options. The arcade room features games such as Dueling Hoop Fevers and Air Hockey, while the loft space offers six flat screen TVs, board games, poker, pool, and a karaoke system.

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Set a short drive from the wonders of Walt Disney World, this five-bedroom home is a brilliant base for a holiday of theme park thrills and Florida sunshine. After a day of coasters and characters, you can chill out in the covered backyard with its private pool, which is the perfect place for some downtime.


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

Explore the 232 most perfect homes in our collection

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Most popular homes in Osceola County

Magic Retreat

Magic Retreat

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Wonder Mansion

Wonder Mansion

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Wonderland Mansion

Wonderland Mansion

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Strawberry Sunrise

Strawberry Sunrise

  • 18 guests

  • 6 bedrooms

Polk County, Florida

The Scholar's Shanty

The Scholar's Shanty

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Floridian Fun

Floridian Fun

  • 14 guests

  • 4 bedrooms

Four Corners, Osceola County

Florida Adventure

Florida Adventure

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Orange Vista

Orange Vista

  • 18 guests

  • 6 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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