Family unpacking cars and greeting each other in front of vacation home

Enjoy a unique stay at the Bear's Den Resort

Vacation Home Capital

Vacation Home Capital of the World

Kissimmee, Florida is the Vacation Home Capital of the World and with more than 30,000 homes to choose from, it’s no wonder where we got the name from.

Vacation homes are more than just your average accommodations. These properties are located in gated communities that have an array of unique amenities such as prestigious golf courses, incredible restaurants, extreme pools and water parks, and more. Not sure where to get started? Use this page as a guide to all your questions and we’ll help out along the way!

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A beautiful vacation home rental in Kissimmee

Vacation Home Rentals: Ultimate FAQ

Explore the endless possibilities for extraordinary vacation homes in Kissimmee: the Vacation Home Capital of the World, each with a unique twist tailored to exceed your getaway needs.

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vacation home, kissimmee
Family of four each sitting on a lounge chair by the pool
A fire pit outside a Kissimmee vacation home

Jeeves Vacation Rental

What's Your Kissimmee Vacation Home Style?

What does your dream vacation home look like? Take our quiz and discover your vacation home style.

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Vacation home at dusk.

End your day in a luxurious vacation home

Comfort, Amenities & More

From the comfort of your vacation home, you’ll have access to these amenities plus the coziness of home. With private pools, luxury kitchens, and full bedrooms and on-suite bathrooms for everyone, these properties make for the perfect home base while you’re visiting Central Florida.

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Vacation Home Capital