Rent Kissimmee Homes with Swimming Pools

We selected the 73 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Kissimmee

Sunshine on the Lake

Sunshine on the Lake

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Get ready for a fantastic vacation at this apartment set on a resort in Florida. The communal amenities here are great.

A Rockin' Time Machine

A Rockin' Time Machine

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This brand new vacation rental is a stunning 4 bedroom, 3 bathroom property with a pool. The cozy beach house is located in the sought-after Storey Lake Resort, making it the perfect destination for an unforgettable vacation.

An Ocala of Ocala

An Ocala of Ocala

  • 16 guests

  • 5 bedrooms

Osceola County, Florida

This brand new single-family home boasts six bedrooms and five bathrooms, including a bedroom on the ground floor. The home features an equipped kitchen, washer/dryer, and a game room in the garage.

Yachts & Yacht Houses

Yachts & Yacht Houses

  • 15 guests

  • 4 bedrooms

Campbell, Osceola County

This beautiful newly furnished and decorated single-family home boasts 5 bedrooms and 5 bathrooms, with 2 bedrooms located downstairs. Equipped with a fully stocked kitchen, washer and dryer, internet, and cable, this home has everything guests need for a comfortable stay.


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

Explore the 73 most perfect homes in our collection

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Most popular homes in Kissimmee

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

The Black Marble

The Black Marble

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

Key To The Palm

Key To The Palm

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

The Skyline

The Skyline

  • 15 guests

  • 4 bedrooms

Osceola County, Florida

Halfnote

Halfnote

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

Paradise on the Shore

Paradise on the Shore

  • 12 guests

  • 5 bedrooms

Osceola County, Florida

View all

Check upcoming rates & availability for Kissimmee 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 Kissimmee. 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 Kissimmee Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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