Book Luxury Short Stay Rentals in Kissimmee

We selected the 99 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

Cottonwood & Palm

Cottonwood & Palm

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

This brand new single family home features five bedrooms and five bathrooms, with two of the bedrooms located downstairs. The fully-equipped kitchen and private game room provide plenty of entertainment options for guests.

The Sea Dragon

The Sea Dragon

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This brand new vacation rental condo is located in the Storey Lake Resort and offers guests a fantastic vacation experience. The condo features two bedrooms and two bathrooms, including a king bedroom with an en-suite bathroom and a second bedroom with a full bed, twin bed, and sofa bed.

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

This brand new 5-bedroom, 4-bathroom vacation rental with a pool is located in the Storey Lake Resort, providing an unforgettable vacation. The bedrooms consist of two king bedrooms, one king suite, one bedroom with a full and twin bed, and one bedroom with a bunk bed twin over full with a twin trundle bed.

Hurricanes in Summer

Hurricanes in Summer

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This brand new vacation rental boasts 4 bedrooms and 3 bathrooms with a private pool. Situated in Storey Lake Resort, guests can enjoy the convenience of being located close to Disney attractions, Disney Springs, malls and Walmart.


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

Explore the 99 most perfect homes in our collection

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Most popular homes in Kissimmee

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Canyoneer

The Canyoneer

  • 11 guests

  • 4 bedrooms

Osceola County, Florida

The Osteria

The Osteria

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

The Walt Disney World Express

The Walt Disney World Express

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

A View to a Dream

A View to a Dream

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

Bulletproof Blue

Bulletproof Blue

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Coral Reef Dreams

Coral Reef Dreams

  • 10 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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