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.
Magical Vacation Homes
With over 300 uniquely-designed properties just miles from Walt Disney World® and the rest of Orlando’s best theme parks, you’ll be sure to find the ideal rental for your vacation needs at Magical Vacation Homes.
Reunion Resort Vacation Home Rentals
Reunion Resort Vacation Home Rentals are the only Official Vacation Home Rental Program of Reunion Resort and therefore the only company which can provide full and unlimited access to all resort amenities. This includes the water park and pools, golf courses, tennis center, spa, restaurants and 24-hour guest services.
Magic Village Views
Welcome to the Magic Village Views, Trademark Collection by Wyndham. The property is located in an elegant gated community and offers three and four-bedroom fully furnished private luxury villas where each home has a complete kitchen, washer, dryer, indoor and outdoor living space with BBQ grills.
Plus Vacation Homes
Choose one of 24 Luxury Villas for your vacation in Kissimmee. All Villas come with a private pool and spa. All rooms have a smart TV with cable to help entertain or relax guests.
Jeeves Florida Rentals
Jeeves Florida Rentals makes trips to Orlando a luxury vacation for the whole family. Their resort-style homes, upward of 12 bedrooms, provide accommodations for up to 32 people with home amenities including bowling alleys, home theaters, arcades, and private gyms, making these homes perfectly designed for family reunions and group gatherings.
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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
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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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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