Everywhere > USA > Florida > Orlando Kissimmee
Orlando Kissimmee Villas & Luxury Vacation Rentals
Luxury Villa Rentals for 2+ people
WE'RE HERE TO HELP! CONTACT US.
Your Guide to Orlando and Kissimmee Villas
Located just west of Orlando, Kissimmee is famous for its historic Downtown, its great golfing, and, of course, its proximity to the Walt Disney World Resort. And with their family-friendly designs and their ample space, Kissimmee villas are the ideal way to enjoy your time in the Magical Kingdom.
Kissimmee is named after the Kissimmee River, which connects to Lake Tohopekaliga. The name is generally translated to mean “long water.” Kissimmee was first founded in 1887 as a quiet cattle town. The opening of Walt Disney World in 1971 saw the area boom, with hotels and villas popping up all around.
Today, Kissimmee is known as the premiere place to stay for a perfect Disney vacation. But it’s also maintained its historic charm, with sites like the Osceola County Historical Society Pioneer Village standing as a testament to its cattle-ranching past.
Rental Escapes makes renting a luxury villa in Kissimmee easy. First, choose your travel dates. Next, select your party size. From there, your Rental Escapes Villa Specialist will happily present you with the best available Kissimmee villas for your group. After, your Concierge customizes your trip, including transportation, chef service, excursions, Disney tickets, and more.
Kissimmee Villa Rentals
Designed with families in mind, Kissimmee villa rentals offer a wealth of amenities that guests love. Game rooms, private pools, lanais, themed bedrooms – everything you need to create the most magical Disney trip ever.
Kissimmee villas can be found all around the area, including the famous Reunion resort, with its water park and golf courses; in the Soltera Resort, with its resort-style clubhouse; and in the nearby Ritz-Carlton Orlando, with its Greg Norman golf course.
No matter where you stay, expect fun Kissimmee villas and a short distance to Walt Disney World. You can also expect 5-star service, including from your Rental Escapes Concierge.
Kissimmee Disney Villas
Located just 6 miles from Disney, Kissimmee Disney Villas offer the most fun and convenient ways to enjoy the park. They include:
Space Palace: Located in the Reunion Resort, Space Palace offers a true luxury Disney experience. It features a large games room, a sprawling private pool with a spillover spa, several themed bedrooms (including a space room), and more. Plus, it’s all tied together with a stunning and sophisticated interior design.
Fantasy at the Bear’s Den: Set in the Bear’s Den, Fantasy has everything you need for endless fun. There’s a home cinema, a superhero-themed arcade, a billiards and poker room, and more. There are also seven well-appointed bedrooms, including princess- and galactic-themed bedrooms for the kids.
Wonderland at Reunion: From the moment you step inside the grand two-story entrance, Wonderland will take your breath away. With a refined contemporary style, this is one of the best-looking Disney villas you can find. There’s also a Lost Boys-themed room, a Mad Hatter’s room, and a Mickey Mouse-themed room.
Luxury Villas near Kissimmee
Located in the Ritz-Carlton Orlando, these luxury villas near Kissimmee set a new standard for fine living near Disney:
The Elysian: Overlooking Grande Lakes and the Greg Norman Signature Golf Course, The Elysian is 4,800 square feet of pure luxury living. Everything here is made with the finest materials, from the marble counters to the naturally-lit bedrooms. There’s also a large pool area by the lake for you to enjoy.
The Arcadian: With a mix of contemporary and classic styling, The Arcadian offers a private oasis in the heart of the Ritz Carlton. There’s a large kitchen, a beautiful living and dining room, an upstairs gallery, a private plunge pool, and more. A superb choice for smaller groups of 6 or less.
Kissimmee Vacation Villas
Designed to maximize relaxation and fun, these Kissimmee vacation villas offer families unforgettable experiences:
Bliss at the Bear’s Den: With fun details around every corner, Bliss offers endless possibilities. Relax in the open-concept living room. Enjoy hours of fun in the games loft. Take a dip in the private pool, or unwind in the spillover spa. There’s something here for the whole family to love.
Tee it Up at Villatel: A golf lover’s dream, Tee it Up features a golf simulator, a bowling alley, two game rooms, and more. There are also themed bedrooms, a private gym, and a cinema. Coupled with a gourmet kitchen and a pool with a mini waterslide, and you have the ultimate family villa.
Slalom at Villatel: Featuring a ski simulator and a ‘hotel lobby’ theme, Slalom is a unique vacation villa. There’s a large private pool for you to enjoy with a mini waterslide, as well as an outdoor barbecue and dining area. Inside, there’s an additional games room and an upstairs loft with even more games. A great choice for up to 28 guests.
Kissimmee Villas FAQ
What are the Entry Requirements for Disney World?
To enter Disney World, you’ll need a valid date-based ticket. Even if you have an annual ticket, you may still need to make reservations for busier days. A Park Hopper ticket will let you visit multiple parks per day. Be sure to bring a Photo ID when you arrive. You can also link your tickets to the My Disney Experience App, and use MagicBands for park entry, purchases, and Lightening Lanes. Your Concierge is happy to provide you with more information.
How to Travel to Kissimmee?
Most travelers to Kissimmee will fly into Orlando International Airport. From there, it’s just a 17-mile (20-30 min) drive to Kissimmee. You can also drive to Kissimmee from the I-4 West, US-192, or via Florida’s Turnpike North from Miami. Kissimmee also has an Amtrak station if you want to take the train. Your Concierge can help with airport transfers, rental cars, and any other transportation needs.
How to Get Around Kissimmee?
The best way to get around Kissimmee is by rental car. Kissimmee is very car-friendly, and a car rental will allow you to see more of the surrounding area. There are also daily shuttles from the Reunion Resort and the Soltera Resort to Disney World. Your Concierge can help with rental cars, private drivers, shuttles, and more.
Best Time to Visit Kissimmee?
Peak season in Kissimmee is from December to April, then again from June to August. The weather is mild and sunny, and the parks and attractions are in full swing. This is the most popular time to visit though, so book early.
Shoulder season is from April-June and mid-August to early October. There are smaller crowds since most kids are in school, but the weather is still comfortable. If you’re able to go at this time, you’ll find some great deals as well.
Off-season is from mid-October to mid-December. The lines are shortest at the park, and there’s still pleasant weather. However, there’s a higher chance of storms, and some attractions may be closed for maintenance. There are also fewer seasonal events. Still, this is when you’ll find the best deals for Kissimmee villas.
Is Kissimmee Safe?
Kissimmee is considered very safe. Our Kissimmee villas are located in gated resorts with 24/7 security, and the Disney parks are also very well-maintained and patrolled.
Best Things to Do in Kissimmee?
Visit the Walt Disney World Resort: Home to the Magic Kingdom, EPCOT, Hollywood Studios, and the Animal Kingdom. There’s something here for everyone to love.
Go to Universal Orlando Resort: This is where you’ll find The Wizarding World of Harry Potter, Islands of Adventure, and Volcano Bay Water Park. Another must-visit.
Visit SeaWorld Orlando and Aquatica: Enjoy marine animal encounters, thrilling rides, and a top-rated water park. A great place to cool down.
How’s the Food in Kissimmee?
Kissimmee’s food scene is diverse and family-friendly. You’ll find plenty of great BBQ, fresh seafood, and Cuban and Puerto Rican cuisine, as well as fun vintage and themed restaurants. Within the resorts, you’ll find great upscale dining in Reunion, more casual fare near the Solterra Resort, and luxury cuisine at the Ritz-Carlton, including the Michelin-Starred Knife & Spoon. Disney World also has its own diverse array of dining options, including themed dining and international flavors at EPCOT. If you prefer to stay in, your Concierge can arrange private chef service and villa pre-stocking on any of our Kissimmee villas.
How’s the Weather in Kissimmee?
Spring in Kissimmee is warm and comfortable, with average temperatures of 65–85°F (18–29°C). Rainfall is moderate, around 2–4 inches (50–100 mm) per month, but humidity starts to rise.
Summer is hot, humid, and rainy, with temperatures averaging 75–95°F (24–35°C). Daily afternoon thunderstorms bring 6–8 inches (150–200 mm) of rain per month, but they’re usually short-lived. Expect high humidity and feels-like temps over 100°F (38°C).
Fall brings cooler but still warm weather, with average temperatures of 65–85°F (18–29°C). Rainfall drops to about 2–4 inches (50–100 mm) per month, and humidity starts to ease. It’s one of the best times to visit, with fewer crowds and pleasant evenings.
Winter is mild and dry, with average temperatures of 50–75°F (10–24°C). Rain is minimal at 2–3 inches (50–75 mm) per month, and humidity is low, making it the most comfortable season for outdoor activities.
Book a Kissimmee Villa with Rental Escapes
If you’re hoping to visit this beautiful part of Florida, Rental Escapes can elevate your Kissimmee villa rental into a true luxury experience.
Our portfolio includes the finest Kissimmee villas, including Disney villas, luxury villas, vacation villas, and more.
Your Rental Escapes Reservations Expert can find the best luxury villa for your group, and your Concierge personalizes your trip to create the ultimate Kissimmee villa experience.
Contact us today to book your next dream holiday!
- Antigua vs St Lucia |
- Barbados vs The Bahamas |
- Cap Cana vs Casa de Campo vs Punta Cana: Dominican Resorts |
- Punta Cana vs Los Cabos: Family vacations |
- Kauai vs Maui vs Oahu vs The Big Island: Hawaiian Islands |
- Punta Mita vs Puerto Vallarta |
- Provence vs. Tuscany |
- Playa Del Carmen vs Cabo vs Punta De Mita: Mexican Vacations |
- Anguilla vs St. Barts |
- Montego Bay vs Ocho Rios: Nightlife |
- Saint Martin vs Sint Maarten: Five Difference |
- Tryall Club Vs Round Hill: Montego Bay |
- Jamaica vs. Barbados
- Antigua |
- Bahamas |
- Barbados |
- Belize |
- British Virgin Islands (BVI) |
- Cayman Islands |
- Costa Rica |
- Croatia |
- Greece |
- Italy |
- Jamaica |
- Los Cabos |
- Riviera Maya |
- Saint Martin |
- St. Barts |
- Turks & Caicos