Book Luxury Short Stay Rentals in Kissimmee

We selected the 97 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Kissimmee

The Oceanaire

The Oceanaire

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

This brand new vacation rental condo is situated in the stunning Storey Lake Resort, offering breathtaking views of the nearby lake. The cozy condo boasts three bedrooms and two bathrooms, including a king bedroom with an en-suite bathroom and two additional bedrooms with a full bed and twin bed in each.

Coral Reef Blue

Coral Reef Blue

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

This beautiful single-family home boasts 5 bedrooms and 5 bathrooms, with 2 bedrooms conveniently located on the first floor. The fully equipped kitchen and screened private pool make it perfect for families and groups alike.

Paradise on the Shore

Paradise on the Shore

  • 12 guests

  • 5 bedrooms

Osceola County, Florida

This brand new vacation rental in Storey Lake Resort is perfect for a luxurious getaway. With 5 bedrooms and 4 bathrooms, this property can accommodate large groups.

A View to a Dream

A View to a Dream

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

This brand new single family home boasts 5 bedrooms and 5 bathrooms, with 2 bedrooms conveniently located on the first floor. The fully-equipped kitchen and game room offer plenty of entertainment options, while the private screened pool and spa provide a relaxing retreat.


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

Explore the 97 most perfect homes in our collection

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Most popular homes in Kissimmee

An Ocala of Ocala

An Ocala of Ocala

  • 16 guests

  • 5 bedrooms

Osceola County, Florida

Hidden in the Sunbelt

Hidden in the Sunbelt

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Florida's Seashell

Florida's Seashell

  • 15 guests

  • 4 bedrooms

Osceola County, Florida

Cottonwood & Palm

Cottonwood & Palm

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Floridian Dream

Floridian Dream

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

Yachts & Yacht Houses

Yachts & Yacht Houses

  • 15 guests

  • 4 bedrooms

Campbell, Osceola County

Casa Rosita

Casa Rosita

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Ode to Summertime

Ode to Summertime

  • 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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