Kissimmee vacation rentals
Our award-winning collection of Kissimmee vacation rentals promise an effortless stay, close to the world-class parks and attractions.
Best Kissimmee vacation rentals
Our luxurious Kissimmee villas and vacation homes are located in the heart of Orlando’s top resorts, including Reunion Resort, Storey Lake, the Bear's Den golf community, Windsor Hills, Windsor Palms, Solara Resort, and more. This award-winning collection invites guests to enjoy the comfort of exclusive home living, with the option of personalized Concierge Services to create unforgettable vacation experiences.
Perfect for couples, families of all sizes, and multi-generational groups, our vacation homes provide the ultimate Orlando getaway. Whether you’re enjoying the lavish interiors, relaxing by your private pool, or taking advantage of on-resort amenities and nearby attractions, our Kissimmee villas offer luxury and year-round relaxation.
Conveniently located near Old Town Kissimmee, you’ll find local attractions like the Twin Oaks Conservation Area and world-class golf clubs. Orlando’s world-famous theme parks are also just a short drive away. For those flying in, our villas are only 14.8 miles from Orlando International Airport (MCO), ensuring maximum convenience for your stay.
Popular Vacation Rentals
The primary airports serving the Kissimmee area include:
Orlando International Airport (MCO): Located approximately 14.8 miles northeast of Kissimmee, Orlando International Airport is the largest airport in the region and offers a wide range of domestic and international flights.
Orlando Sanford International Airport (SFB): Situated approximately 47 miles northeast of Kissimmee, Orlando Sanford International Airport serves as an alternative option for travelers, offering both domestic and international flights.
Orlando Executive Airport (ORL): Located about 22 miles northeast of Kissimmee, Orlando Executive Airport primarily serves general aviation and private aircraft.
Getting around Kissimmee, Florida as a tourist is generally convenient, although having access to a car is advisable for greater flexibility and convenience. Here are some key points to consider:
Car Hire: A rental car remains the most convenient and practical way for our guests to explore Kissimmee, Greater Orlando and the Central Florida area. Having a car provides flexibility in navigating the region's top sights and attractions. Explore our private care rental options for a carefree stay.
Kissimmee road network: Kissimmee boasts well-maintained roads and highways, making it relatively easy to navigate. Major thoroughfares such as Interstate 4 (I-4) and the Florida Turnpike provide efficient routes to popular destinations including theme parks, shopping centers, and downtown areas.
Public Transportation: While public transportation options such as Lynx buses and SunRail trains serve the greater Orlando area, including parts of Kissimmee, they may not offer the same level of convenience and accessibility compared to having a personal vehicle.
Alternative Transportation: In addition to car rentals, tourists may also consider ride sharing services like Uber and Lyft for shorter trips within Kissimmee and neighboring areas. As an optional extra, our dedicated Concierge team are on hand to arrange airport transfers, private transportation, theme park shuttles and more.
Walt Disney World: 13.3 miles (22 minutes' drive). Disney's EPCOT: 13.4 miles (28 minutes' drive). Disney's Typhoon Lagoon water park: 13.6 miles (26 minutes' drive). Disney's Hollywood Studios: 13.7 miles (24 minutes' drive). Disney's Blizzard Beach water park: 14.8 miles (25 minutes' drive). Disney's Magical Kingdom: 15.2 miles (25 minutes' drive). Universal Studios: 18.2 miles (26 minutes' drive). Universal Volcano Bay water park: 18.2 miles (26 minutes' drive). Universal's Wizarding World of Harry Potter: 18.9 miles (27 minutes' drive).
Please note car journey times can vary, depending on the time of day. We advise setting off to the parks first thing, to avoid any unwanted congestion and to ensure you make the most of your day at the parks.
To book discounted attraction tickets contact our Concierge team today!
Situated in the heart of Central Florida's Osceola County, Kissimmee offers unparalleled access to Orlando's most iconic treasures. With world-class destinations like Disney World at your fingertips and waterparks, golf courses, designer shopping and dining just moments away, Kissimmee offers a quintessential gateway to the thrills and spills of Central Florida.
Dive into the heart of the Everglades or soak up the sunshine at Kissimmee's renowned resorts, boasting world-class water parks and championship golf courses. Unleash your adventurous spirit with an off-road adventure at Gatorland or with an exhilarating airboat tour through alligator-infested waters.
Nearby, experience the excitement of Old Town's amusement park or take a thrilling ride on the world's tallest Skycoaster at Fun Spot America. From perfecting your swing on world-class golf courses to indulging in Orlando's premier attractions and shopping destinations, Kissimmee promises pure excitement and adventure!
Kissimmee Fine Dining
Looking to splash out or celebrate a special occasion? These renowned Kissimmee dining establishments offer exceptional culinary experiences you won't easily forget.
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Charley’s Steak House & Seafood Grille - Cuisine: Steakhouse, Seafood: $$$$
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7593 Chophouse - Cuisine: American: $$$$
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Old Hickory Steakhouse - Cuisine: American, Steakhouse: $$$$
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Boston Lobster Feast - Cuisine: Seafood: $$$$
Budget-friendly meals out in Kissimmee
For memorable meals out that won't break the bank, these popular Kissimmee restaurants make great dining options, away from your vacation home.
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Villa Italiano Chophouse - Cuisine: Italian: $$ - $$$
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Los Amigos Mexican Grill & Tequila Bar - Cuisine: Mexican: $$ - $$$
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Drafts Sports Bar & Grill - Cuisine: American, Bar, Gastropub: $$ - $$$
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Medieval Times Dinner & Tournament - Cuisine: American: $$ - $$$
Local Breakfast eateries
These popular, budget-friendly breakfast spots offer a variety of breakfast and brunch options to suit, making them ideal for starting your day right in Kissimmee!
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Express Cafe - Cuisine: Latin, Cafe, Venezuelan: $
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Woodsby's Cafe - Cuisine: American, Cafe, Diner: $
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Krispy Kreme - Cuisine: American, Fast Food: $
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IHOP - Cuisine: American, Diner: $
Wherever you choose to dine out in Kissimmee, you will find a great selection of all-American favorites and tempting world food cuisine options, to satisfy all tastebuds and budgets.
Discover Walt Disney World ResortDive into the magic of Walt Disney World Resort, where enchanting attractions, thrilling rides, and beloved characters come to life across four enchanting theme parks.
Experience Universal Orlando ResortImmerse yourself in the wizarding world of Harry Potter, embark on thrilling adventures, and experience blockbuster movie attractions at Universal Orlando Resort.
Visit Old Town KissimmeeStep back in time at Old Town Kissimmee, where vintage charm meets modern entertainment, with classic car shows, live music, shopping, and memorable vacation dining experiences.
Embark on an Airboat TourTake an exhilarating airboat tour through the picturesque wetlands of Kissimmee, where you can encounter native wildlife like alligators, birds, and turtles.
Play some GolfTee-off from the renowned public courses of Celebration Golf Club, Falcon's Fire Golf Club, Remington Golf Club, Kissimmee Bay Country Club, and Kissimmee Golf Club.
Experience a Hot Air Balloon RideEnjoy a new viewpoint of Kissimmee and Orlando, from the uplifting front row seat of a hot air balloon ride! The experience is perfect for a special occasion or grand romantic gesture.
Enjoy Fun Spot AmericaExperience adrenaline-fuelled rides, go-kart racing, arcade games, and family-friendly attractions at Fun Spot America, a thrilling amusement park in the heart of Kissimmee.
Kissimmee villas with luxury Concierge
In addition to exclusive privacy and home comfort, our award-winning Kissimmee vacation homes offer optional Concierge Services for a truly unforgettable vacation. Whether you need private car hire, airport transfers, grocery packs, or a private chef, we’ve got you covered. Our services also include babysitting, golf tee times, in-villa spa treatments, attraction tickets, and more, all tailored to enhance your Kissimmee getaway.
Resort rentals with pools in Kissimmee
Many of our Kissimmee resort homes feature their own private pool, alongside luxury resort amenities. Whether you're looking for a sleek infinity pool, a scenic pool with a hot tub overlooking golf fairways, or a family-friendly pool with an all-weather cage, our collection offers something for everyone.
Many of our villas with pools also include private poolside kitchens, dining areas, wet bars, garden games, and relaxation zones with sun loungers. From small splash pools to large pools with waterslides and lazy rivers, we cater to all preferences and budgets. With endless Floridian sunshine, your Kissimmee villa with a private pool will become a highlight of your stay!
Explore Kissimmee villas with pools
Kissimmee villas for families
Perfectly placed for soaking up a sun-drenched vacation close to the parks, our collection of Kissimmee villas are ideal for families and multigenerational groups. With spacious open concept living spaces with luxury kitchens for carefree dining, accompanied by games rooms and covered lanais with summer kitchens for alfresco dining, our Kissimmee villas set the scene for effortless entertaining and R and R with family and friends.
Family villas with themed rooms in Kissimmee
For families looking to stay, our beautiful Kissimmee vacation homes with themed bedrooms promise to provide an equally epic and unforgettable base for year-round vacations. Equipped with additional private villa amenities, ranging from private pools and home theaters to epic games rooms, private gyms and even indoor bowling alleys, our Kissimmee family villas set the scene for a fun multigenerational getaway.
Our Kissimmee villas for families with themed rooms also promise a seamless vacation experience, with access to luxury on-resort amenities and optional Concierge services to enhance your stay.
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Kissimmee villas for groups
Our Kissimmee villas are perfect for large groups, offering spacious living areas and plenty of room for everyone to relax. Whether you’re planning a family reunion, a friends’ getaway, or a special celebration, these villas provide the ideal base for your stay. With multiple bedrooms, fully equipped kitchens, private pools, and game rooms, our villas offer everything you need for an unforgettable group vacation.
These villas are also designed for comfort and entertainment, with features like outdoor kitchens, alfresco dining areas, and relaxing lounges. After a day at the parks or exploring Orlando, unwind by your private pool or enjoy the villa’s luxury amenities, making every moment of your stay special.
Located just minutes from top Orlando attractions like Walt Disney World and Universal Studios, our Kissimmee villas offer the perfect combination of convenience and privacy. You’ll be close to everything Orlando has to offer, from world-class theme parks to shopping and dining.
For added convenience, we offer optional Concierge services to personalize your stay, whether you need airport transfers, attraction tickets, or private chefs. Our team is here to ensure your group has an effortless and memorable vacation experience.
Explore group-friendly villas in Kissimmee
