Twenty miles south of Orlando, Kissimmee is a hub for family vacations in Florida. Walt Disney World Resort is a 15-minute drive from the lakeside city which makes an equally convenient base for LEGOLAND Florida, Peppa Pig Theme Park, Cape Canaveral, and the Atlantic coast. The “Vacation Home Capital of the World” isn’t short on thrilling rentals with themed bedrooms to delight toddlers through to grandparents. These are the coolest Kissimmee vacation rentals for families in Florida’s entertainment capital.
Traveling to Orlando, Universal Studios, or Disney World? Check out Matador’s guides to the best places to stay in the area:
One of the best Kissimmee vacation rentals for multigenerational families, this exceptional Vrbo has a Moana-themed bunk room and a Mickey and Minnie’s Jungle Safari suite. The remaining rooms come with upholstered beds and private bathrooms. Gather downstairs to finesse your air hockey skills in the Star Wars games room or partake in Disney rewatches over popcorn in the movie theater. The screened-in patio has a pool and spill-over hot tub.
Eleven guests, five bedrooms Price: $880 per night
Designed for anyone who never wants to grow up, this family-friendly rental has a swashbuckling bedroom to rival the Pirates of the Caribbean ride. The rest of the home is elegantly appointed with heavy wooden moveables and antique collectibles. The pool has a slide, fountains, and splash pads to offset Florida’s baking-hot summers. Back inside, you’ll find a games room stocked with air hockey and ping pong.
Fourteen guests, six bedrooms Price: $361 per night
Hanging off the edge of the championship-rated Highlands Reserve Golf Club, this golfer’s paradise has a landscaped pool with a second-floor lanai overlooking the tropical reserve. A safety net and pool alarm system provide peace of mind for parents. The garage now serves as the games room, leaving space for two cars on the driveway. Disney, Orlando Tree Trek Adventure Park, and Old Town are 30 minutes or less.
Twelve guests, five bedrooms Price: $326 per night
This family-friendly Vrbo with themed kids’ bedrooms might be even more exciting than getting a selfie with Mickey. Little ones can toss coins for Moana, Spiderman, Indiana Jones, and Star Wars while teens – and let’s be honest, adults – will be googly-eyed for the gamer’s bedroom. The house has a private pool, games room, and home cinema for everyone to enjoy. Kissimmee Airport is a five-minute drive and you’re spoiled for choice in terms of restaurants and attractions.
Twenty-two guests, 10 bedrooms Price: $369 per night
While many Kissimmee rentals cater to dynasties, this top-rated Vrbo from a premier host is tailored for smaller clans of eight. Minutes from Medieval Times, this single-story home has traditional decor and one Mickey Mouse-themed bedroom. The screened-in pool and hot tub back onto a peaceful reserve in the Whispering Oaks community. It’s close to all the attractions yet a far cry from bustling Orlando.
This luxurious house at Kissimmee’s Bella Vida Resort is full of Floridian charm. It has a private pool with enviable views of the lake plus a spacious sun deck with barbecue facilities. If you need a change of scene, dive into the resort pool or take the kids on a nature walk. There’s a games room with arcade basketball and two themed bedrooms for children. As for the location – Tinker Bell, Peppa, and Co are practically neighbors.
Seventeen guests, eight bedrooms Price: $264 per night
Another whopping big Vrbo in Kissimmee for large groups, this family-friendly vacation house has Harry Potter, Minions, and Disney Princess-themed rooms to squabble over. Venture over to the dark side in the home cinema and see how many rewatches you can tick off. The pool and hot tub overlook the resort lake, a welcome sight after a thrill-packed day at theme parks and airboating alligator-infested swamps.
Twenty-three guests, ten bedrooms Price: $316 per night
It looks like a regular suburban home on the outside but the Once Upon A Time villa is a castle indoors. The open-concept lounge has a sumptuous settee overlooked by a state-of-the-art kitchen. Kids can sleep in enchanted carriage beds or Spiderman bunks whereas teens will be starry-eyed for the Star Wars suite. There’s a Mickey Mouse-themed games room and heated pool plus complimentary use of the resort’s water slides and lazy river.
Twenty guests, nine bedrooms Price: $468 per night
This 10/10 rental is one of the closest Vrbos for Disney World. It has a swimming pool and jacuzzi sunken on a screened porch with ample seating for a post-theme park debrief. The airy master bedroom has an en suite with a heart-shaped corner tub, perfect for a bubble bath. Cook anything you want in the state-of-the-art kitchen or rent a barbecue grill. Baby essentials are provided free of charge.
Longtime fans will be “Buzzed” to see posters from classic Disney and Pixar movies plastered all over this lakeside townhome. Whether for kids or adults, all beds are wrapped in cartoon linens while shower curtains will inspire a morning sing-a-long. The rental is part of a luxury resort with five pools and a clubhouse where kids can trade trivia and practice their cannonballs. Don’t be afraid of the mice in the kitchen – they’re old friends.
Aye aye, the more the merrier at this mammoth holiday home for multiple families with a taste for the high seas. Besides cartoon-themed kids’ bedrooms, adults can fall asleep on the sets of Game of Thrones, Buffy the Vampire Slayer, Stranger Things, and Breaking Bad. There’s a private Mickey Mouse clubhouse for tots and a pirate ship movie theater with space for everyone to come aboard. Not forgetting a lovely pool with a projector screen.
Thirty-eight guests, 15 bedrooms Price: $595 per night
