Book Luxury Short Stay Rentals in Kissimmee

We selected the 74 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 Kissimmee

 King's Castle

King's Castle

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

Looking for a holiday that caters to the whole family? This resort condo might just be it.

Casa Rosita

Casa Rosita

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Just a short drive from Disney World, this home makes it easy to enjoy the magic of Florida. You can spend your days exploring the nearby attractions and you’ll find all the amenities you could need within easy reach.

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.

Body of Evidence

Body of Evidence

  • 15 guests

  • 4 bedrooms

Kissimmee, Osceola County

This beautiful brand new single-family home in the Storey Lake community is equipped with five bedrooms and five bathrooms, with two bedrooms conveniently located downstairs. The kitchen is fully equipped and the house also features a screened private pool and spa, as well as a game room for entertainment.


We selected the top 3% holiday homes in Kissimmee Short Stay Rentals

Explore the 74 most perfect homes in our collection

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Most popular homes in Kissimmee

The Canyoneer

The Canyoneer

  • 11 guests

  • 4 bedrooms

Osceola County, Florida

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Palms Over Water

Palms Over Water

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

A Rockin' Time Machine

A Rockin' Time Machine

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

For You Love

For You Love

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Electric Ocean

Electric Ocean

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Parkside Magic

Parkside Magic

  • 11 guests

  • 4 bedrooms

Osceola County, Florida

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Check upcoming rates & availability for Kissimmee Short Stay Rentals


Frequently asked questions

Browse our curated collection of Short Stay Rentals in Kissimmee. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Kissimmee luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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