Kissimmee …. The Vacation Home Capital of the World® 

A place to do as little or as much as you’d like! If you dream it, you can do it here. Shake hands with a mouse. Dine with kings and queens. Zip line over alligators. Play it cool with some penguins. Blast off into outer space. Fly through the air on boats, balloons, and broomsticks. Let your inner night owl loose at concerts as they return, restaurants and outdoor entertainment. 

Take your pick of more than 70,000 accommodation options.  Unique to Kissimmee is our portfolio of vacation home rentals. Currently, our area boasts over 50,000 vacation home properties, ranging from 1-15 bedrooms.  Maybe that’s why we’re called the Vacation Home Capital of the World®.

Kissimmee’s ultra-luxe vacation home rentals can have all the bells and whistles, including: gourmet kitchens, themed rooms, movie theatres, bowling alleys, holiday décor, and concierge services. The best part? For groups and extended family visits, vacation home rentals are available to suit every taste, style and budget.

 With such an incredible assortment of accommodation options and easy access to world-famous theme parks and attractions, state-of-the-art golf courses, world-class dining, and relaxing outdoor experiences, Kissimmee provides snowbirds with everything they could want and need for a memorable getaway vacation in  Central Florida.

Snowbird Clubs & Activities

One great resource for snowbirds is the City of Kissimmee Parks & Recreation for Seniors. There’s lots of activities to get involved in and meet your fellow snowbirds.

Activities include Texas Hold’em, Ladies Craft Club, TOP (Take the Pounds off sensibly), Basic Bridge, Quilting, TOHO Friends, and Cribbage.

Getting to Kissimmee

Flying

Snowbirds have a wide variety of choices when it comes to flying to Central Florida with direct service into both Orlando International Airport, as well as Orlando’s Sanford International Airport from various gateways.

Air Canada currently offers year-round service from both Toronto and Montreal with connectors available from across Canada.

Westjet currently offers year-round service from Toronto. Calgary and Edmonton are scheduled to restart at the end of November, as well as seasonal service direct from Halifax. Connectors are available from across the country. 

Air Transat resumed service in September with direct flights from both Toronto and Montreal. Quebec City flights also return mid-December and both Halifax and Moncton in February.

Looking to save?  Why not try out one of the new, low-cost carriers introducing service into Orlando’s Sanford International Airport.

Swoop is currently offering direct flights from Toronto, Hamilton, Winnipeg, and Edmonton.  Register on their website to receive great updates on seat sales, typically on Fridays … also known as Fri-yays!

Flair Airlines is currently offering direct flights from Toronto, Montreal, Kitchener/Waterloo, and Ottawa.

Driving

With the reopening of the land borders between Canada and the U.S., many snowbirds opt to drive instead of fly. 

Driving from SW Ontario/GTA:

Two routes: I-77, crossing over at Windsor (17.5hrs) or I-75 (about 100kms longer, 19.5hrs), crossing over at Niagara Falls/Buffalo. 

By Rail: Amtrak provides rail service to Kissimmee, as well as Orlando, Winter Park, and Sanford. The Kissimmee station is the closest one to Walt Disney World® Resort.

Weather

The winter months generally provide the most pleasant temperatures, where the rainfall is low and even the cooler nights warm up into beautiful days. (But it’s still a good idea to pack a light jacket.)

As spring approaches, temperatures start to warm up. Though still on the pleasant side, rainfall does start to increase and temperatures can fluctuate.

The months of July through September are the rainy season in Central Florida. The temperatures can often rise into the 90s (Fahrenheit) (30s Celsius) and afternoon thunder showers are a common occurrence. Evenings can be on the pleasant side, especially if there is an afternoon rain.

If visiting Kissimmee in the summer, be sure to pack lightweight clothing and items to protect you from the sun and rain.

As fall approaches, the average temperature and rainfall start to decrease. On any given day, it can be hot enough for a day basking in the sun or cool enough for a lightweight jacket.

No matter what time of year, it’s recommended you always wear sunscreen when enjoying the Florida sun.

Terrain and Landscape

Kissimmee's landscape showcases live oak hammocks, freshwater marshes, and open prairies.

The Kissimmee Chain of Lakes includes numerous lakes, from Cypress Lake in the north to Lake Kissimmee in the south.

World famous beaches are only a short drive away, with Cocoa (60 minutes) and Daytona (90 minutes) on the Atlantic coast and Clearwater (2 hours) on the Gulf Coast.

Accommodations and Where to Stay

Whether it’s a family getaway, mini-stay, or long stay in Kissimmee, snowbirds can take their pick of more than 70,000 accommodation options to find their ideal place in the sun.

We have everything from amazing 4-star resorts to hotels, vacation home rentals ranging in size from cozy 1-bedroom cottages at Margaritaville Resort Orlando to as large as 15-bedroom mega-mansions, as well as a number of campgrounds and RV parks. There’s truly something for every style and budget!  

A fantastic lead-in property, the Celebration Suites offers affordable, spacious, family-friendly 1- and 2-bedroom suites with full eat-in kitchens. Located steps from Old Town Kissimmee and Fun Spot America, filled with shopping, dining, and entertainment options. Pets welcome. 

Caribe Cove is a fabulous resort offering all the comforts of home-away-from-home in spacious 2- and 3-bedroom villas with enclosed patios or balconies and offers the ideal spot for morning coffee or evening cocktails.

Relax in the comfort of a luxurious 3- or 4-bedroom, elegantly furnished townhome at Magic Village Yards offering all of the services and facilities of a resort with the comfort and privacy of a vacation home.

Why stay in a hotel when you can have all of the space and comfort of a home in either a 2- or 3-bedroom spacious villa at Tuscana Resort while still enjoying all of the amenities of a resort.

Melia Orlando Celebration offers the best of both worlds. An upscale hotel fusing together stylish comfort and location just a short distance from all the magic with standard hotel rooms, 1- and 2-bedroom suites available.

Enjoy a complimentary full hot breakfast, access to 3 pools, and a poolside bar n’ grill at the new Springhill Suites Orlando Lake Buena Vista South. Guest suites offer a seamless blend of style and function complete with sofa for extra living space, microwave, and mini-fridge.

Reunion Resort & Golf Club has it all! Situated in a gated community surrounded by three championship golf courses, when it comes to accommodation, this full-service resort offers luxurious hotel rooms, 2- and 3-bedroom villas, as well as high-end, vacation home rentals ranging in size from 4- to 15-bedrooms.

The best of both worlds! The Westgate Vacation Villas Resort & Spa provides all the comforts of a fully furnished home with accommodations ranging in size from cozy studios to spacious 2-bedroom villas which can sleep up to 10 people. A great choice for having family visit during the winter. This resort offers a multitude of on-site amenities and dining options and is minutes from the world-famous theme parks.

Vacation Home Rentals

Imagine waking up to a picturesque lake view or watching the sunrise on the golf course from your own private balcony of your vacation home rental. Whether you're looking to spend a quiet weekend getaway in a 2-bedroom villa, have end-of-summer family gathering in a 14-bedroom mansion, or a long stay getaway far from the harsh Canadian winter, Kissimmee has you covered!

With more and more vacation home rentals being added each year, we've compiled 10 reasons why you should choose Kissimmee as your home-away-from-home. 

Elite Vacation Homes Offering 2- to 7-bedroom villa and vacation home rentals centrally located to restaurants shopping, theme parks, and area attractions.

Alexander Holiday Homes offers 2- to 7-bedroom fully equipped vacations homes to suit every style and budget.

Orlando Rent-A-Villa offers a great selection of 1- to 15-bedroom villas and homes centrally located to shops, restaurants, and entertainment options. 

Global Resort Homes prides themselves in offering high quality vacation home rentals in Kissimmee at affordable prices. From 2-bedroom condos to spacious and luxurious 9-bedroom homes, you're sure to find accommodations that will suit your every need. 

Jeeves Florida Rentals A luxury vacation for the whole family await! These resort-style homes, upward of 12 bedrooms, provide accommodations for up to 32 people with home amenities including bowling alleys, home theatres, arcades, and private gyms, making them perfectly designed for family reunions and group gatherings. If you’re looking for a more intimate setting, they also offer 2- and 3-bedroom condominiums rentals.

Campgrounds & RV Parks

Tropical Palms Resort Above and beyond being an RV park and campground, this is a fantastic resort offering unique accommodation such as colourful cottages, cabins, tiny houses, vacation campers, and even yurts!

Find old Florida with rustic giant oak trees and big bass fishing in a relaxing and comfortable environment at Boggy Creek Resort & RV Park

Sherwood Forest RV Resort is the perfect place for either a seasonal stay or weekend getaway.

Attractions & Sights

Kissimmee is just a wave-of-the-wand away from four world-famous theme parks. Explore “How to Travel to all the Major Theme Parks from Kissimmee” to spend less time on the road and more time on rides. 

• Walt Disney World® Resort
• Universal Orlando Resort
• SeaWorld® Parks & Resorts™ Orlando
• LEGOLAND® Florida Resort

Glide the headwaters of the Florida Everglades on an airboat, taking in this unique wetland ecosystem. Take a thrilling ride to “Stalk Gators at 40 MPH” with one of our many airboat companies.

• Boggy Creek Airboat Adventures
• Spirit of the Swamp Airboat Rides
• Wild Florida
• Wild Willy’s Airboat Tours

Take in the sunrise, theme parks, and natural beauty of Central Florida from a hot air balloon.

• Bob’s Balloon Rides
• Thompson Aire

Traverse over hills, through mud puddles, and pass real alligators from the comfort of a 12-foot high, off-road monster vehicle on the Stompin’ Gator Off-Road Adventure at Gatorland.

Become a fighter pilot for a day by flying in a legendary WWII P-51 Mustang at Stallion 51.

Snap the perfect #slothie (sloth selfie) or relaxing drive through the new safari at Wild Florida.

Head down memory lane during the Saturday Nite Car Cruise at Old Town Kissimmee, one of America’s longest running weekly car shows and cruises.

Defy gravity on Fun Spot America-Kissimmee’s Mine Blower Roller Coaster, a wooden coaster with a 360-degree barrel roll and 11 instances of air time.

Travel back in time to the 11^th century at Medieval Times Dinner and Tournament, where a jousting tournament between knights and a feast fit for a king ensues.

Experience breathtaking 360-degree views of Central Florida on The Eye at ICON Park with sights of theme parks, lakes, lush landscape, and on a clear day, views of Cape Canaveral.

Culture & Entertainment

Up for dinner and a show? Just let us know what you’re hungry for. Take a seat and pull up a chair as our dining shows proudly present your dinner: Kissimmee Dinner Show Round-Up 

Step back into the 1800s at the Pioneer Village at Shingle Creek and tour an authentic Cracker house, citrus packing house, and blacksmith’s shop, as well as replicas of a train depot, schoolhouse, and historic church.

Explore an authentic Native American Village at Boggy Creek Airboat Adventures to learn how original Americans cooked, hunted, and lived many years ago or experience an airboat ride where you can spot gators and more wildlife.

Take in Kissimmee’s heritage, which includes the Monument of States, the state’s oldest operating courthouse, and a walking tour of historic Downtown Kissimmee.

Food & Dining

There’s so much to choose from in the Kissimmee area when it comes to dining and all things culinary. Whether you are looking for brunch, lunch, fine dining or something casual, you'll find plenty of options.  Here are just a few examples:

• Sip on fresh Florida wines at Island Grove Winery Company at Formosa Gardens, a sustainable winery and microbrewery. The surrounding eight-acre botanical garden grows fruits, vegetables, and herbs while maintaining sustainable agriculture practices. Enjoy a bottle of wine and charcuterie board in the vineyard in the evening with a great view of the fireworks from the theme parks overhead.
• House of Blues Gospel Brunch is good for the stomach and soul. Listen to local talent perform traditional and contemporary Gospel songs, all while enjoying an all-you-can-eat buffet featuring breakfast favourites, carving stations, and southern specialties.
• Feast on flavours for every palate at Disney Springs®, from world-class cuisine crafted by five James Beard Award-winning chefs to a breezy lunch, or just a light bite from a food truck.
• The Promenade at Sunset Walk is a beautiful outdoor entertainment district, home to casual eateries, fine dining, entertainment options, regular events, and retail shops with new storefronts and restaurants still to come. You’re sure to enjoy the fare and flair of Cuba at Estefan’s Kitchen, owned by world-renowned singer Gloria Estefan and her husband Emilio, one of many unique dining and entertainment options sure to please. 

Festivals & Events

There are many festivals and events taking place in Kissimmee and the surrounding area for snowbirds to enjoy during the winter months. Here’s just a small sample of what you can look forward to:

1. Walt Disney World® Resort’s 50^th Anniversary is well underway with an 18-month celebration.
2. In April, take your mark for the RAM National Circuit Finals Rodeo in Kissimmee. Champions from all over the U.S. compete for a chance to make it to the Wrangler National Finals Rodeo in Las Vegas.
3. In mid-June, roll up your jeans and stomp grapes at the Annual Harvest Festival at Lakeridge Winery. At this weekend-long event, peruse local artwork and tour the winery.
4. For a spook-tacular party for all ages, Mickey’s Not-So-Scary Halloween Party transforms Magic Kingdom® Park into a happy, haunted haven for Halloween fun on select evenings from late August through October.
5. During select nights in September and October, spine-chilling moments lurk around every corner with terrifying haunted houses, outrageous live shows, and scary creatures at the award-winning Halloween Horror Nights at Universal Orlando Resort.
6. In October, yodel, dance, and celebrate the fall season at Oktoberfest at Celebration Town Center. The event celebrates old-world German traditions with sing-alongs and hayrides.

Sporting Events

With three professional sports teams nearby, sports fans won’t be disappointed in the Kissimmee region:

• Watch Central Florida Major League Soccer team, Orlando City Soccer Club, tear up the field from March through November.
• NBA fan? Take in an Orlando Magic home game. If you time it right, maybe you’ll get to see them battle it out against our very own champion Toronto Raptors on April 1, 2022. Tickets are on sale now!
• If you're a Blue Jays fan, it's never too early to plan for spring training camp in their new facility located just over an hour away in Dunedin! Visit their website for the schedule and to purchase tickets.

Shopping

Many snowbirds love to shop during their winters away and Kissimmee has some great options. Check out these malls, shopping centers and outlet malls:

• Orlando Vineland Premium Outlets® and Orlando International Premium Outlets®
  
  Premium Outlets offer two distinct and incredible outlet shopping locations featuring designer and brand name stores with savings of 25% to 65% every day. Orlando Vineland Premium Outlets, with 160 stores, is located less than a mile from Walt Disney World® Resort. Orlando International Premium Outlets, with 180 stores, is located minutes from Universal Orlando Resort.
• Lake Buena Vista Factory Stores
  
  Lake Buena Vista Factory Stores is known among savvy consumers as one of Central Florida’s “best-kept secrets for outlet deals,” offering factory-direct premium quality merchandise at savings up to 75% off and sometimes more.
• The Loop
  
  An easy-to-navigate, one-stop shopping center, The Loop offers stores such as Kohl’s, Ulta, American Eagle Outfitters, and Yankee Candle all within walking range.
• The Mall at Millenia
  
  The Mall at Millenia has 150 shops and restaurants. Take advantage of being pampered with a complimentary personal stylist session. A perfect 2-hour shopping experience. Visit their website to book your appointment before you leave!

Fitness & Outdoor Recreation

There are plenty of ways for snowbirds to keep active in Kissimmee, with golf as one of the favourite pastimes -  there are 22 courses in the area! There’s also great fishing, canoeing and kayaking, as well as other outdoor activities:

• Golf
  
  The fairest of fairways and the greenest of greens. Any way you slice it, the 22 18-hole golf courses in Kissimmee are some of the best in the Sunshine State. Elevate your game to the next level at one of our renowned golf academies, such as the David Leadbetter Golf Academy at Omni Orlando Resort at ChampionsGate or The Golf Academy at Celebration Golf Club.
• Fishing
  
  If trophy bass are what you’re looking for, cast a line in Kissimmee, “A Bass Fishing Mecca.” The experts at Jay’s Bass Bustin Guide Service or Orlando Fishing Guide will take you to all the best fishing spots. 
• Paddle 
  
  Paddle beneath towering cypress trees by kayak, canoe, or stand-up paddleboard at The Paddling Center at Shingle Creek.

Lifelong Learning

For snowbirds who like to keep their minds active during their winters away, Kissimmee has great options for classes, courses and other learning opportunities:

• The University of Central Florida’s Learning Institute for Elders (LIFE) program has been offering weekly lectures for seniors since 1991.
• At Celebration Lifelong, courses are offered purely for the joy of learning— no academic credit or certificates are awarded.
• Valencia College provides credit courses that are open to anyone interested in the subject matter.

Health Care & Medical Facilities

Osceola County offers many convenient medical center locations that provide the utmost of care. These facilities provide testing, outpatient care, and emergency services.

• Osceola Regional Medical Center

• Poinciana Medical Center
• AdventHealth Kissimmee
• AdventHealth Celebration
• Orlando Health St. Cloud

What's Nearby & Excursions

If you're looking for local excursions to mix things up while spending your winter in Kissimmee, you'll find it's well located to visit many nearby Florida attractions. Here are just a few suggestions:

Kennedy Space Center

Explore the gateway to space exploration at Kennedy Space Center Visitor Complex, located just an hour-and-a-half from Kissimmee. Get face to face with shuttles such as the famous Space Shuttle Atlantic and get on a first-name basis with astronauts in the U.S Astronaut Hall of Fame.

Victory Casino Cruise

Victory Casino Cruise, located just an hour from Kissimmee, sails seven days a week, twice daily, and features Vegas-style gaming with craps, roulette, blackjack, mini-baccarat, three-card poker, ultimate Texas hold'em, and the region's only sportsbook.

Real Florida Adventures

Real Florida Adventures offer a full day excursions to the coasts including transportation with a central pick up and drop off point in Kissimmee. Kennedy Space Center Visitor Complex, deep sea fishing, swimming with manatees, and a day at the beach are hot spots. They’ve got it all!

Canadian Deals & Offers

Snowbirds can visit our Experience Kissimmee Deals & Discounts page here for the latest deals and offers.

Cruise Ports

If you're a snowbird looking to enjoy a cruise during your stay in Florida, Kissimmee is within easy driving distance of two major cruise ports:

• Port Canaveral Cruise Port Terminal on the East Coast, I-4 East, 94kms (59 miles): Carnival, Disney, Norwegian Cruise Line, Royal Caribbean
• Tampa Cruise Port on the West Coast, I-4 West, 117kms (73 miles): Carnival, Holland America, Norwegian Cruise Line, Royal Caribbean

Safety

Find covid safety tips and advice for your trip to Kissimmee here:

https://www.experiencekissimmee.com/safe-vacations 

Cost of Living

Kissimmee’s cost of living is below the average for the U.S. and Florida.

https://www.payscale.com/cost-of-living-calculator/Florida-Kissimmee provides an overview of how different categories of expenses relate to the national average.

LGBTQ

Kissimmee welcomes snowbirds and other travellers who are members of the LGBTQ+ community. The following resources are available:

• LGBT+ Center Kissimmee is a satellite office of the LGBT+ Center Orlando, Inc.:
  https://thecenterorlando.org/homepage-kissimmee/
• The Sheriff’s office launched a safe place program:
  https://www.osceolasheriff.org/safe-place-program/
• Find a list of LGBTQ friendly businesses in the Greater Orlando area:
  https://thepridechamber.org/

See why Canadian snowbirds love Kissimmee:

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