Hello. At Ocean Florida we use cookies to give you the best possible
experience. By visiting our
site, you agree to our cookie policy Close white logo close

The Ultimate Guide to the Best Villas in Kissimmee

  • By Christopher da Costa
  • Published 15 August 2023
  • Revised 04 September 2023
The Ultimate Guide to the Best Villas in Kissimmee
  • By Christopher da Costa
  • Published 15 August 2023
  • Revised 04 September 2023
The Ultimate Guide to the Best Villas in Kissimmee
  • By Christopher da Costa
  • Published 15 August 2023
  • Revised 04 September 2023

Kissimmee, Florida is celebrated as the Vacation Home Capital of the World. And for good reason. With its close proximity to the world-famous theme parks, glorious year-round sunshine - and of course a wealth of vacation home communities - it truly is the ideal location to call home on a Florida holiday...

Picking a Location: Where in Kissimmee should you stay?

Picking a location for your villa rental in Kissimmee is all about preference. Would you like to be a stone’s throw from magical moments at Walt Disney World? Does the idea of blissful nature settings put your mind instantly at ease? Or, maybe you’re just after a bit of everything? Well, with the following villas to rent in Kissimmee, the possibilities are endless.

Best Kissimmee Villas for Families

Windsor Hills

A stay at Windsor Hills guarantees an excellent choice for families. With a fun water park, children’s splash pad, a large castle-themed kids' playground, an entertaining games room, and a 40-seater cinema, entertainment abounds for children and adults alike. What’s more, Windsor Hills showcases a delightful selection of themed bedrooms, from Harry Potter’s enchanting wizard world to a Frozen winter wonderland and the intergalactic realm of Star Wars, which are sure to capture the imagination of young minds.

Adding to the allure of this family-friendly resort, Windsor Hills is the closest villa community to Walt Disney World, eliminating the need for long car rides. Enjoy a short, carefree 3-mile drive to Walt Disney World and make the most of your family holiday.

Discover our top tips for Florida family holidays here.

Best Kissimmee Villas for Nature

Bella Vida Resort

Set amidst 15 acres of glorious lakes, Bella Vida Resort is the ultimate in relaxation. This serene resort offers a range of attractions for the nature lovers in the group, from picturesque walking trails to spectacular Italian gardens, as well as a breathtaking 25-foot waterfall. Plus, with its scenic picnic area, lunchtime can be a feast for the eyes as well as the stomach.

Veranda Palms Resort

Steeped in the breathtaking beauty of Shingle Creek National Park, Veranda Palms Resort is a great choice for guests seeking a tranquil and scenic holiday. It is also situated at the headwaters of Florida’s nature king, the Everglades. But aside from the wealth of nature surrounding this Kissimmee villa, the resort itself boasts a crystalline swimming pool where you can cool off for the day while admiring the overlooking beauty of calming lakes and lush woods. Then, if you’re feeling adventurous, there are several walking and biking trails to get the adrenaline pumping.

Explore more of the Best Florida Villas for a Nature Retreat here. 

Best Kissimmee Villas for Resort Pools

Encore Club

Get ready to dive into adventure at an assortment of Encore Club pools. The main resort pool offers a host of poolside comforts, such as loungers, cabanas, and great food and drink. But you can really make a splash at the 10-acre waterpark. This unique addition incorporates thrilling water slides, a lazy river, and a designated splash pad for kids, making your Kissimmee villa rental holiday even more memorable.

Storey Lake Resort

Located in the heart of Kissimmee, Storey Lake Resort is the ideal place to cool off from the scorching heat. It’s home to a sparkling pool, a lazy river, and a jacuzzi. Plus, with their children’s splash park, kids can run wild (with supervision of course) between water slides, spray features, and interactive water play areas. 

Read more about Orlando Villas Resorts with the Best Pools here.

Best Kissimmee villas for Games Rooms

Reunion Resort

This highly sought-after villa community in Kissimmee takes 'games room' to another level. Whether you want to be immersed in your very own neon-lit 80s-inspired arcade dreamland, get competitive with rounds of pool and air hockey, or even take to the bowling alley (yes, within your home) Reunion Resort can provide. 

Windsor Hills

For a great variety of gaming needs, Windsor Hills is a great choice for Kissimmee villa holidays. This popular community near Walt Disney World Resort offers games rooms with something for everyone, from video game consoles to pool tables and foosball. You will also find board games and card games for more traditional gaming. Plus, some villas here even feature classic arcade games, such as Pac-man and Donkey Kong for that hit of nostalgia.

Find more Kissimmee Villas with Great Games Rooms here.

Best Kissimmee Villas for Themed Bedrooms

Windsor Island

Step into an enchanting world of playful Minions, Marvel superheroes, and the iconic Mario Brothers during your stay at Windsor Island. Decked floor-to-ceiling with vibrant themes bound to spark the curiosity of your youngsters, these rooms will be an adored haven for your kids. With an array of other beloved themes, including Mickey Mouse, LEGO, and enchanting Disney princesses, Windsor Island offers an abundance of choices to keep young hearts utterly captivated.

Reunion Resort

There may be a few fights for bedrooms at Reunion Resort, after all, there are many to choose from. Cosy up Encanto style in your own floral chamber, board the Hogwarts Express bunk bed in the magically designed Harry Potter room or enter a galaxy far far away as you slip into your very own space capsule bunk bed fit for a Jedi. Or maybe you fancy being one with nature in the treehouse-themed bedroom? At Reunion Resort, themed room villas definitely add that touch of enchantment to your stay.

Read more about Orlando Villas with Awesome Themed Bedrooms here.

Best Kissimmee Villas for Luxury

Solara Resort

Nothing screams luxury more than your own private pool with a spillover spa or lounging by the lagoon-style resort pool, cocktail in hand. At one of Kissimmee’s newest communities, you will feel like royalty every day. Solara Resort also features a wealth of 'keep fit' options, from a state-of-the-art fitness centre to basketball and volleyball courts. And while the contemporary styling and granite countertops of your own kitchen invite you to unleash your inner chef, there is also an elegant on-site restaurant for when you want to be treated. Then, while the kids do a bit of gaming in the teen/tween hangout area, you can soak up your own private time at the on-site coffee shop.

Reunion Resort

There's a reason Reunion Resort Villas keeps popping up on this list. For a truly indulgent Florida holiday, you will find one of the best villas in Kissimmee here. Ranging from one-bedroom cosy retreats to superb 12-bed mansions, they come equipped with private pools and spas, an outdoor BBQ grill, and some even offer games rooms and in-home cinemas for that added extravagance. All this is set on a manicured estate spanning 2,300 acres in Kissimmee, which is also home to three PGA golf courses, crafted by legendary icons of the sport: Jack Nicklaus, Tom Watson, and Arnold Palmer. If swimming is more your sport, however, then the 5-acre water park awaits. And when the stomach rumbles at the end of the day, take your pick from seven exquisite on-site restaurants offering a range of cuisines to suit your taste.

Learn more about our Top Luxury Villa Communities here.

Best Kissimmee Villas for Gated Communities

Windsor Palms Resort

If peace of mind is top of the priority list when choosing your holiday villa in Kissimmee, then Windsor Palms Resort may just be the one. Every visitor is required to sign in at the 24/7 security entrance prior to gaining access through the secure gate, enabling you to embrace tranquillity as readily as the leisurely days spent by the resort's serene pool. And as the day winds down, rest assured of a peaceful night's sleep in your cosy multi-bedroom villa equipped with all the comforts of home.

Find more Gated Villa Community Holidays in Florida here.

Best Kissimmee Villas for Large Groups

Encore Club

Featuring an array of 10 to 12-bedroom residences, the Encore Club at Reunion effortlessly caters to groups of up to 24 individuals within a single mansion. These villas are thoughtfully furnished to comfortably accommodate such a sizable group, boasting expansive dining tables, large living areas replete with spacious sofas, and ample outdoor seating for when the festivities spill over to the outdoor swimming pool area. What’s more, the opulent homes at the Encore Club at Reunion are replete with cutting-edge games rooms, cinema spaces complete with sumptuous recliners, and captivating themed bedrooms, ensuring a wealth of entertainment options to enthral a large gathering within the confines of the villa.

Best Kissimmee Villas for All Interests

Paradise Palms Resort

When it comes to deciding on your Kissimmee villa rental, going with something for everyone is key. Luckily, Paradise Palms Resort has just that. Although being conveniently located close to all of Orlando’s big draws, the resort itself features an array of amenities. The highlight is the fantastic clubhouse, which features a large lagoon-style pool, a hot tub, and a tiki bar and grill where you can enjoy snacks poolside. Fitness fanatics can get their fill at the fitness centre or take to the courts for a game of tennis, basketball, or volleyball, while kids can jump between the arcades, movie theatre, and playground for hours of fun.

Windsor Hills Resort

You have already seen Windsor Hills on our list of best family villas and best villas with games rooms - all while combining superb facilities with a prime location beside Walt Disney World, ensuring Windsor Hills is a top choice for all around interests. Better yet, you can enjoy the privacy of your own villa pool or take advantage of the resort’s lagoon-style pool with a water slide for added thrills. And remember, you can also enjoy a range of amenities at the clubhouse, where you can challenge the family to a game of tennis or wind down with a movie in the 40-seat movie theatre. 

Learn more about the Best Orlando Area Villa Communities for Every Type of Traveller here.

5 Popular Kissimmee Villa Exact Homes

Windsor Hills – Ocean 245

The immaculate open plan design of this home allows for quality family time, whether in the kitchen preparing a scrumptious meal or chilling out on the plush sofas in the living room. You can also spend hours of fun in the well-equipped games room or take a dip in your very own private pool. And when it’s time to venture out, the resort itself has plenty of amenities, including a 40-seat movie theatre for those family movie nights. Better yet, if your dream is to have Mickey and the gang as neighbours, this Windsor Hills home is on Walt Disney World’s doorstep, offering guests a magical stay like no other.


Emerald Island – Ocean 209

Surrounded by a 300-acre conservation area, your blissful holiday awaits at this Emerald Island villa. The dreamy pool deck is the ideal place to admire the surrounding beauty, but even more jaw dropping sights await inside the villa. Immerse yourself in your favourite movies with the 100-inch projector screen equipped with surround sound, then take to the games room for a round of pool. And when it’s time to hit the hay, large spacious suites will ensure a great night’s sleep. 

Encore Club – Ocean 544

Amazing Kissimmee villas should be accessible to all, that’s why this 8-bedroom home is specifically designed with wheelchair users in mind. From the zero-entry pool with a convenient pool lift to the zero-entry shower and lowered basin in the ground floor room, it has everyone covered. 

Although conveniently located close to Orlando’s world-class attractions, the themed Disney games room and SeaWorld- inspired bedroom will have you feeling like you’re there already. With space for up to 16 guests, this villa is perfect for larger family holidays and the resort has plenty to suit both the little ones and grown-ups alike, including a waterpark, spa services, and plenty of sporting options.

Storey Lake - Ocean 290

Just 5 miles from Walt Disney World, a charming 6-bedroom home awaits. Revel in the allure of a pool and spa facing the southern sun, where you can luxuriate on rattan lounges. Step inside to find reprieve on plush sofas, where leisure takes the form of indulging in a large LED TV or engaging in spirited competition within the thrilling London-themed games room. Ascend upstairs, where another living area awaits, complete with a pool table to amplify the merriment. With distinct lounging spaces, individual bedroom televisions, and a plethora of entertainment choices, everyone can savour their private sanctuary during leisurely days.

Solara - Ocean 052

Immerse yourself in the world of elegance within this exquisite 9-bedroom, 6-bathroom abode nestled in Solara Resort. Beyond its private pool, fully equipped kitchen, and stylish decor lies an interstellar adventure waiting to unfold. The Star Wars-themed games room beckons, offering an array of exhilarating games, including foosball, air hockey, rolling ball arcade, and video games. For a lighter diversion, venture into the living room for some engaging pool table action, or step outside to luxuriate in the spillover spa amidst the open air. 

Discover our Top 10 Exact Home Florida Villas here. 

Factors to Influence Your Kissimmee Villa Decision

If there was ever a time to book your dream Stateside getaway, this would be it. Our fabulous Ocean Explorer package is now available to everyone who books an Orlando or Kissimmee holiday and includes a range of exclusive benefits.

How do free tickets to The Wheel at ICON Park sound? Or your chance to explore International Drive with seven days of free access to the I-Ride Trolley? And we’ve even thrown in a free visit to the oldest and best dinner magic show in town, the Outta Control Magic Comedy Dinner Show.

Plus, with our flexible payment plans, your dream Kissimmee villa holiday doesn’t even need to break the bank. Spread the cost up to 36 months in advance, secure in the knowledge that everything is ATOL and TTA protected.

Overall, choosing the perfect villa in Kissimmee can significantly enhance your holiday experience. It allows you to embrace the magic of Florida’s enchanting attractions while enjoying comfort, luxury and above all, quality family time.

Ready to live in luxury and play in paradise on the doorstep of Florida’s best gems? Check out our Villa Package Holidays in Florida.

Enjoyed This Article?
Now choose what happens next...
Looking to Book
a Holiday?

This button will take you to a short form where we'll ask about your destination and preferences. If you don't like filling in forms simply give us a call on 01708 989 371 and we'll be happy to help you.

Receive Our
Exclusive Offers

Join our email to receive exclusive offers and airline sales direct to your inbox. Unsubscribe anytime (but why would you want to?)