Reunion Resort 15000 Kissimmee vacation villas and rentals

Best Kissimmee vacation rentals

Our luxurious Kissimmee villas and vacation homes can be found in the heart of Orlando's most coveted resorts, including Reunion Resort, Storey Lake, the Bear's Den golf community, Windsor Hills, Windsor Palms, Solara Resort, and beyond. Our award-winning collection of Kissimmee villas, vacation homes and condo rentals invite guests to indulge in exclusive home comfort. Complimented by optional Concierge Services, our Kissimmee villas are here to create unforgettable vacation experiences.

Designed to appeal to couples, small-large families and multigenerational groups, our vacation homes provide the optimum Orlando getaway. Whether you're wining and dining away in the lavish interiors, soaking up the Florida sun by your private pool, or diving into the luxury on-resort amenities or nearby attractions, our Kissimmee vacation homes offer a haven for luxury and year-round relaxation.

Conveniently situated within easy reach of Old Town Kissimmee, you'll discover a treasure trove of local attractions, including the enchanting Twin Oaks Conservation Area and world-class golf clubs, whilst the magic of Orlando's first-class theme parks are within easy driving distance from your villa. For those flying into Orlando, our villas and vacation homes are a mere 14.8 miles from Orlando International Airport (MCO), ensuring the ultimate convenience for year-round stays.

A map of Orlando, Florida

Things to do

  • Cinderellas castle at Walt Disney World in Orlando
    Discover Walt Disney World Resort
    Dive into the magic of Walt Disney World Resort, where enchanting attractions, thrilling rides, and beloved characters come to life across four enchanting theme parks.

  • Universal Studios Orlando park
    Experience Universal Orlando Resort
    Immerse yourself in the wizarding world of Harry Potter, embark on thrilling adventures, and experience blockbuster movie attractions at Universal Orlando Resort.

  • A young boy and a woman on a carousel
    Visit Old Town Kissimmee
    Step 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.

  • An airboat tour in the Everglades
    Embark on an Airboat Tour
    Take an exhilarating airboat tour through the picturesque wetlands of Kissimmee, where you can encounter native wildlife like alligators, birds, and turtles.

  • Golfer rests a ball on a tee
    Play some Golf
    Tee-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.

  • A hot air balloon ride in Kissimmee Orlando Florida
    Experience a Hot Air Balloon Ride
    Enjoy 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.

  • A family enjoying a roller coaster
    Enjoy Fun Spot America
    Experience 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.

  • American alligators in the Florida Everglades
    Take a trip to Gatorland
    Get up close and personal with Florida's iconic wildlife at Gatorland, where you can watch alligator wrestling shows and even zip line over alligator-infested waters!

  • Two people enjoying a meal with wine at a restaurant
    Savor a Medieval Times Dinner & Tournament
    Experience the excitement of a medieval jousting tournament, while feasting on a delicious four-course meal fit for royalty at Medieval Times Dinner & Tournament.

Luxury Vacation Rentals

A curated portfolio of the best vacation homes and villas in the world’s top destinations

Travel Planners

Experienced vacation rental and villa experts to help you find the perfect home

Concierge & Support

Enjoy 5-star hotel concierge services and dedicated local support with every stay

A chef wearing a white jacket smiles as he holds a plate of food

Kissimmee villas with luxury Concierge

Aside from exclusive privacy and home comfort, our award-winning collection of Kissimmee vacation homes also offer optional Concierge Services - for guests seeking an optimum vacation experience. From private car hire, airport transfers and grocery packs to private chef, babysitting, golf tee times, in-villa spa treatments, attraction tickets and more, our tailor-made services are designed to enhance your Kissimmee vacation in every way.

7 bedroom vacation rentals with pickleball access in orlando florida bears Den 27

Resort rentals with pools in Kissimmee

Alongside luxury resort amenities, many of our Kissimmee resort homes also feature their own private pool. Whether you're seeking a sleek infinity pool, a scenic pool with hot tub overlooking the golf fairways or an all-weather pool cage for the family, our wide collection invites you to dive right into a memorable stay.

Complementing many of our Kissimmee villas with pools, you will find private poolside summer kitchens, dining areas, wet bars, garden games and of course relaxation areas and sun loungers. From bijou-size splash pools to sprawling pools with waterslides and lazy rivers, our vast collection caters to all budgets and preferences. With endless Floridian sun to soak up, your Kissimmee villa with private pool promises to become an attraction in itself!

Book with Confidence

With over 100,000 happy guests every year, you can book your next stay with us with total confidence.

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Reunion Resort 32 5 bedroom vacation rentals

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.

The striking facade of Reunion Resort 1500 in Kissimmee, Orlando. Florida

Kissimmee villas for groups

Whether you're looking to soak up the ultimate golf trip, bacholerette break, sports' team stay or corporate getaway, our luxury Kissimmee villas for 20 and 30 guests offer the perfect solution for large groups. Located in luxury resorts just 14-15 miles from Orlando International Airport (MCO), 12.9 miles from the Orange County Convention Center and close to Orlando's world-class stadiums and sporting venues, our Kissimmee resorts with optional Concierge go above and beyond a hotel room stay.

Kissimmee golf villas and vacation homes for sports' teams

Golfing groups can easily find their dream luxury golf villa in Kissimmee. From a golf villa with pool overlooking the fairways, to luxury golf mansions for 20 to 30 guests with private putting greens and indoor golf simulators, our award-winning collection won't disappoint. Our Concierge team are on hand to tailor-make your golf break, with golf carts, tee times, golf coaching and more. Sports' teams are also perfectly catered for, with many of our Kissimmee villas equipped with pools, home gyms, spa facilities and even basketball courts and ski simulators! Located in Kissimmee resorts with first-class sports training facilities, including championship golf courses and state-of-the-art tennis and pickleball centers, active groups have everything they need for experiencing a rewarding break.

Kissimmee villas for corporate stays

Corporate groups of up to 20-30 guests can easily tap into our beautiful corporate-friendly Kissimmee resort homes, conveniently located nearby the Orange County Convention Center. These Kissimmee corporate villas can be rented side-by-side and feature a host of luxury in-house amenities - without a themed bedroom in sight! Our exclusive Kissimmee homes are located in resorts with first-class amenities and business facilities, golf courses and airports, whilst being close to a host of conference centers and team-building activities. Our luxury Concierge services include private catering, transportation to conference centers, attraction tickets, private excursions, in-villa business facilities, on-resort venue hire and more, to create a complete wrap-around Orlando business trip.