Mother and Son Each in Their Own Pool Tube Floaty, Splashing and Playing in the Pool, Enjoying the Beautiful Kissimmee Weather

Make a splash in the pool at a vacation rental in Kissimmee 

Vacation Home Capital

Your Home Base for Adventure and Relaxation

Kissimmee, Florida: the Vacation Home Capital of the World®.

Welcome to the Vacation Home Capital of the World®, where your dream vacation doesn’t just begin—it starts with a splash. Our vacation homes are the perfect mix of comfort and adventure, with warm sunshine and a breeze that practically says, “Come on, let’s go have some fun!” Whether you’re here for family bonding or an epic getaway with friends, you’ll find everything you need to make memories that’ll last.

Tucked away in gated communities with perks that’ll make you feel like royalty—think championship golf, mouthwatering dining, and pools that beg for cannonballs—these homes are your playground. And when you're ready to take on Florida’s year-round sunshine, outdoor adventures are waiting. From airboat rides through the Everglades to peaceful walks along scenic trails, nature’s calling. Plus, you’re just minutes away from world-famous theme parks, shopping, and entertainment.

With over 30,000 vacation homes to choose from, it’s no wonder we’ve earned our title. Not sure where to start? Don’t worry—this guide’s got you covered for a sunshine-filled, excitement-packed getaway that’ll be one for the books.

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A two story Mediterranean style vacation home sits in the back ground, with a pool, chairs and fire pit in the foreground at dusk.
Magical Vacation Homes

Magical Vacation Homes

Vacation Homes in Kissimmee for Spring Break

It won’t be long before spring has sprung, and that can only mean one thing — spring break! Y ou can have everything you’ve ever dreamed of in a vacation, right here in Kissimmee.

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Game room in Bear's Den resort room with pool table

Game room in Bear's Den resort room with pool table

Family unpacking cars and greeting each other in front of vacation home
family with young children enjoying time at a pool at their large vacation home

Relax by the pool with your family at Bear's Den Vacation Home

Top Kissimmee Vacation Home Rentals for Families

Kissimmee has Central Florida’s best selection of family-friendly vacation home rentals.

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Family eating a meal together next to a pool at their vacation home

Find the perfect home-away-from-home with Jeeves Florida Vacation Rental

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