Vacation Home Capital of the World
Make a splash in the pool at a vacation rental in Kissimmee
Your Home Base for Adventure and Relaxation
Kissimmee, Florida: the Vacation Home Capital of the World®
Your dream vacation begins with more than just a place to stay — it starts with endless possibilities for fun and relaxation. 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. When you're ready to embrace Florida’s year-round sunshine, outdoor adventures await — from airboat rides through the Everglades to peaceful walks along scenic trails. Plus, you’re just minutes away from world-famous theme parks, shopping, and entertainment.
With more than 30,000 vacation homes to choose from and a handful of trusty vacation home management companies to guide you, let this be your go-to resource for finding the perfect retreat — whether you're seeking luxury or a cozy hideaway.
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 Rentals
Vacation is about treating yourself to something really special – and Reunion Resort’s vacation homes and condos meet that description perfectly. Each vacation home at Reunion Resort is unique in size and amenities, so you can choose the features and space that fit your family or traveling party’s needs. Home amenities may include a private pool, home theater, game room, themed bedrooms, and more!
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.
Inside the Vacation Home Capital of the World®
Wander into Kissimmee’s most spectacular vacation homes with our “Inside the Vacation Home Capital of the World®” video series. Each episode takes you behind the scenes — from 15,000-sq-ft themed bedrooms and sprawling pools to private bowling alleys, epic game rooms, and serene spa retreats — showcasing luxury designs and unique amenities that redefine what it means to vacation in style.
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"Frozen" themed bedroom in a Kissimmee vacation home
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! You can have everything you’ve ever dreamed of in a vacation, right here in Kissimmee.
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Vacation homes to match everyone's accommodation needs
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
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