Luxury Long Stay Rentals in Kissimmee

We selected the 91 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

Sunshine on the Seaside

Sunshine on the Seaside

  • 11 guests

  • 4 bedrooms

Campbell, Osceola County

This stunning brand new vacation rental features four bedrooms and three bathrooms, including a king bedroom downstairs, a king suite, a full/twin bed bedroom, and a bunk bed with a twin over full and trundle twin bed. Located in the popular Storey Lake Resort, guests will enjoy easy access to Disney, Disney Springs, malls, and Walmart.

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.

Bolu-Bolu Beach

Bolu-Bolu Beach

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

This stunning 2-bedroom, 2-bathroom vacation rental condo boasts breathtaking lake views and is situated in the highly sought-after Storey Lake Resort. The condo is conveniently located near Disney World, Disney Springs, Malls, and Walmart, making it the perfect choice for guests looking to explore the area.

Floridian Dream

Floridian Dream

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

This brand new 4-bedroom, 3-bathroom vacation rental is located in the beautiful Storey Lake Resort and promises a wonderful vacation experience. The property features one king bedroom downstairs, a king suite, one bedroom with a full and twin beds, and one bedroom with a bunk bed full over full + twin trundle.


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

Explore the 91 most perfect homes in our collection

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Most popular homes in Kissimmee

The Skyline

The Skyline

  • 15 guests

  • 4 bedrooms

Osceola County, Florida

Halfnote

Halfnote

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

A History of the Sun

A History of the Sun

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

The Canyoneer

The Canyoneer

  • 11 guests

  • 4 bedrooms

Osceola County, Florida

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Black Marble

The Black Marble

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

The Sun & White

The Sun & White

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

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Check upcoming rates & availability for Kissimmee Long Stay Rentals


Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Kissimmee. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Kissimmee collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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