Vacation Home Rentals
Explore Kissimmee Vacation Rentals
Stay your way in the Vacation Home Capital of the World®.
The ultimate home away from home is a Kissimmee vacation rental. The area offers more than 22,000 professionally managed properties, ranging from affordable, single-family homes to 12-bedroom mansions and luxury villas. With spacious floor plans, private pools, and just about every amenity under the sun, you can enjoy all the comforts of home and then some. Plus, world-famous theme parks are practically in your backyard.
Jeeves Florida Rentals
Spread out in style and get comfortable with these single-family homes.
Spacious homes with multiple bedrooms and bathrooms, roomy common areas, private pools, and big kitchens are the recipe for the perfect vacation. Partners like Jeeves Florida Rentals offer all that and more, including themed bedrooms and game rooms to delight all ages.
The Bear’s Den Resort Orlando
Families and friends can stay under one roof with these multi-family homes.
If you’re visiting Central Florida and seeking lots of bedrooms and fun amenities for all ages, multi-family vacation homes are the way to stay. At The Bear's Den Resort Orlando, private rental homes can comfortably sleep up to 18 people.
Magical Vacation Home
Enjoy luxe lodging in Central Florida with these luxury Villas.
With ultra high-end properties featuring chefs kitchens, private spas, personal concierge service, and more, Kissimmee can accommodate the most lavish of lifestyles. The Isole Villa by Magical Vacation Homes offers a multi-tiered pool with an island for lounging in the sun, and that's just the beginning.
Elite Vacation Home
Making a splash is always a good time!
Many memories are made in the pool, splashing the day away. Elite Vacation Homes offers a range of different vacation home rentals with private pools and some with hot tubs, too.
Magic Village Views
Kissimmee makes everyone feel at home with these fully accessible homes.
Several property management companies offer fully accessible homes with luxury amenities. Companies like Jeeves Florida Rentals offer a range of accessible properties, including ground-level homes with open floor plans for easy navigation.
10 Reasons to Choose a Vacation Home Rental in Kissimmee
With more and more vacation home rentals being added each year, we've compiled 10 reasons why you should choose Kissimmee as your home-away-from-home.Explore More
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!
Surround Yourself with Magic in These Unique Vacation Homes!
With game rooms, bedrooms, and in-house theaters, these vacation home rentals make for a magical place to stay.Explore More
Stay, Work & Play Together in Kissimmee
Pair work with play when you stay in Kissimmee. The Vacation Home Capital of the World® allows you to do it all: work, play, relax, and stay in style!
Explore All Vacation Homes
Find the perfect place to stay for your crew in Kissimmee.
Snapshots of fun adventures in the heart of Florida