Villas in Kissimmee for rent - Definitive Travel Guide
Find and reserve luxury Villas in Kissimmee for rent - Definitive Travel Guide on 5 Star
Best Kissimmee Villa Resorts, Near Disney
Every property is personally inspected for quality, space, and guest experience.
Not sure which villa suits your group in Orlando?
Every enquiry is handled by a single villa specialist. They'll match you to the right property based on your group, dates and priorities.
From first conversation to checkout, the same person stays with you.
- Personalised shortlist (usually 2–3 options)
- Pre-arrival planning & local tips
- 24/7 support during your stay
Explore Orlando villa locations
Our team can help you pick the right area and villa for your group.
Gateway options depend on your villa; your specialist will advise on typical transfer times and the smoothest route.
Nearby shops, dining and day-to-day essentials are usually a short drive in and around Orlando.
Regional highlights vary by route and season; we can suggest realistic timings from your villa shortlist.
Evenings out from local markets to restaurant rows—ask us for curated picks and sensible drive expectations.
Kissimmee and Reunion
Hand-picked villas · local insight · OrlandoDiscover luxury stays within easy reach of Kissimmee and Reunion and the wider Orlando area.
Browse villas near Kissimmee and Reunion →Lake Buena Vista
Hand-picked villas · local insight · OrlandoDiscover luxury stays within easy reach of Lake Buena Vista and the wider Orlando area.
Browse villas near Lake Buena Vista →Winter Park
Hand-picked villas · local insight · OrlandoDiscover luxury stays within easy reach of Winter Park and the wider Orlando area.
Browse villas near Winter Park →Clermont west
Hand-picked villas · local insight · OrlandoDiscover luxury stays within easy reach of Clermont west and the wider Orlando area.
Browse villas near Clermont west →Your Guide to Renting a villa in Orlando, United States
Close to all of the major theme parks
One of the major attractions of Kissimmee is just how close it is to all of the big theme parks. Within around 20 minutes - or less depending on your villa choice - you could be meeting Mickey at Walt Disney World, channelling your inner Harry Potter or Hermione Granger at Universal Orlando, or being splashed by orcas at SeaWorld. The proximity of all the parks to Kissimmee means that you can easily make a number of visits to your favorite theme park, or visit a different one each day.
Things to do in Kissimmee with kids
While Mickey et al are bound to keep your little, and not-so-little, ones entertained, there are also myriad other attractions for the whole family in and around Kissimmee. Along the Orange Blossom Trail, which runs between Kissimmee and Orlando, you'll find Gatorland, where you can get up close and personal to Florida's most famous residents - its alligators. You can wrestle a gator, feed them some special hotdogs, see rare white gators, or even take a zipline across the park to see these magnificent critters from above.
For more animal encounters, pet the cute animals at Green Meadows petting farm for some outdoor time away from the rollercoasters, watch the baseball at Osceola County Stadium, look out for wildlife in its natural habitat at the Disney Wilderness Preserve or take an airboat ride at Boggy Creek.
More things to do in Kissimmee
It's not all about the younger guests at Kissimmee. There is plenty to keep you entertained, happy and well-fed even if you don't step foot inside the iconic Disney Maingate. Head to Old Town Kissimmee where you'll discover a charming olde worlde re-creation of classic Florida, where you'll find a vast array of shops and restaurants as well as the iconic ferris wheel which takes you 86ft in the air above Highway 192. If you visit during the weekend, watch for the classic and muscle cars and trucks which assemble for a drive down Old Town's Main Street.
Visit the museum of military history, jet ski on one of Kissimmee's lakes, take a fishing trip, or dress up and head out to one of Kissimmee's fine dining spots for a culinary treat. Just make sure you make reservations well in advance if there is somewhere really special you want to dine.
Villas in Kissimmee
One of the great things about Kissimmee is there are so many villas to choose from. However, that can also make finding the right villa for you and your family bewildering. That's why we have carefully curated the best 5-star Kissimmee villa collection to make choosing your next holiday easy.
While visiting theme parks can be lots of fun, it can also be very tiring, so it's important to have a home from home to come back to for relaxation at the end of each action-packed day. You'll find villas with every comfort you could want, including private pools and spas, plenty of space for the whole family, games rooms and themed bedrooms. Kissimmee villas come in all sizes so you're sure to find the right property, even if you're travelling in a group of extended family and friends.
The best villa resorts in Kissimmee
If you are keen on exploring the Kissimmee area, but aren't sure exactly where to stay, take a look below at some of the best resorts to choose from in Kissimmee:
Reunion Resort & Spa
From condos to villas, each of Reunion Resort & Spa's accommodation options offer a touch of luxury, while you can enjoy the extensive facilities on the resort including golf on courses designed by legends of the sport, a raft of dining options, a large pool with lazy river and luxurious spa treatments, all within a 10-minute drive of Disney's Maingate.
Windsor at Westside
Strategically placed for all of Kissimmee's attractions, with particularly easy access to SeaWorld and Universal Orlando, the centrepiece of Windsor at Westside is its huge resort pool and splash park. Choose a lounger right at the centre of the pool or relax with a cocktail from the tiki bar.
Windsor Hills Resort
Minutes from Disney, Windsor Hills Resort features an impressive resort pool and waterpark along with its own movie theatre and well-equipped fitness centre. You'll find villas from three bedroom to six bedroom, many their own private pool.
Storey Lake Resort
One of the big draws of Storey Lake Resort is the lake access on offer. You can hire a kayak and head out onto the water for an hour or so. Or, if you prefer your water activities pool-based, you can simply float around the lazy river. There's a choice of homes from two bedrooms up to nine bedrooms, sleeping up to 23 guests.
Paradise Palms Resort
Less than 10 minutes' drive from Disney, Paradise Palms features a walk-in pool, tiki bar and movie theatre. Villa rentals come with their own private pool, and you'll find townhouses with four bedrooms through to six-bedroom detached villas with all the space you need.
Emerald Island Resort
Our handpicked collection of Emerald Island Resort villas are consistently in demand from families who appreciate the upscale resort atmosphere and spacious villas. You'll find villas sleeping up to 14 guests in seven bedrooms. Within minutes from Disney, yet in the heart of a conservation area, Emerald Island offers the best of all worlds.
Choosing your Kissimmee villa
Our 5-star villas in Kissimmee have all been chosen by our travel experts for their convenient locations, their incredible facilities and resort-style feel. So, whichever you choose for your trip, you're sure to be right at the heart of all the theme park action as well as being able to enjoy the facilities in the resorts themselves.
If you do want extra advice on choosing the right villa for you, we love nothing better than helping to ensure you find the perfect accommodation for your family.
Kissimmee Temperature Chart
Ready to find your villa?
Browse our collection or speak to a villa specialist.
Orlando Villa Guides & Inspiration
Helpful guides to plan the perfect Orlando mansion getaway.
Orlando’s Most Sought-After Villa Resorts — A Curated Guide
You’ve decided on a villa in Orlando. Good call. More space, your own pool, room for everyone to breathe between park days. But now comes the question most people get stuck on: which resort?
Windsor Hill Resort Windsor Hill Resort
A cost comparison and experience breakdown for groups of 10+ deciding between vacation mansion rentals and hotel suites.
ChampionsGate Mansions Near Disney: The Complete Guide
Everything you need to know about staying in ChampionsGate — from the Oasis clubhouse to the best mansions for groups.
Orlando, Florida, Villa Holidays – In A Nutshell
‘Laughter is timeless, imagination has no age, dreams are forever’, Walt Disney created a dreamland for us all! Make you and your family’s dreams come true with the holiday of a lifetime, an Orlando Villa Holiday.
ChampionsGate Mansions Near Disney: The Complete Guide
Everything you need to know about staying in ChampionsGate — from the Oasis clubhouse to the best mansions for groups.
Windsor at Westside Windsor at Westside
Champions gate resort is a 1 billion dollar, 900 acre development. This exclusive resort is located with easy access to Orlando international airport, walt disney world theme parks and universal studios.
