In Kissimmee, the Magic Is In the Price of Your Stay

Vacay.ca occasionally publishes content on destinations outside of Canada that our editors believe will be of keen interest to our audience. This article focuses on Kissimmee, noted for its vacation homes and proximity to popular theme parks. For more Florida coverage, venture to VacayNetwork.com.

In our era of relentless inflation, few things can qualify as a bonafide bargain. The vacation homes of Kissimmee fit the definition so perfectly your eyes will bulge — as mine did — when your ears comprehend the price.

It’s $575 USD (about $800 CAD) per night. Not for the usual stays, like a suite with a king bed and pullout couch, or a two-bedroom, two-bathroom unit with a full kitchen and pool in a good location. You get way more than that. Imagine paying $575 (or $2,400 per week) for a 10-bedroom luxury home with high-tech gaming consoles, a swimming pool, hot tub, movie theatre, 85-inch TV, pool table, and two each of fridges, stoves, and dishwashers — on a private golf resort located 15 minutes by car from Disney World. Now you might understand my guffaw when I heard the relative pittance of a cost.

Like most frequent travellers, I’ve had nightmare experiences with rentals from Airbnb or similar companies. In recent years, I’ve switched to looking at hotels first because they have done the work to build consumer trust. When I do search Airbnb it’s for larger accommodations that fit a travelling group and I will pay a premium (which goes against the original thesis of the alternative-housing rage) to avoid the pitfalls of home rentals.

Things are sunnier in Kissimmee, which markets itself as the “Vacation Homes Capital of the World”. With more than 30,000 options, it reputedly has the largest collection of vacation home rentals of any destination on the planet. Experience Kissimmee, the official tourism authority for Florida’s Osceola County, has lent its brand reputation to the vacation home market; vetting properties and partnering with accredited property ownership and management companies to help ensure a problem-free stay for travellers. One of the leaders in Kissimmee is Magical Vacation Homes, which brings group and multigenerational travel a coveted product: affordable luxury in an excellent location.

If it’s your first time at Disney or Universal Studios and you have only a few days and plan to spend the entirety of your visit at the theme parks, then the Orlando hotels tied to those properties are your best options. But for those many travellers, especially Canadians, who are repeat visitors to Central Florida and desire to stay a week or more, a vacation home in Kissimmee is the smarter choice. Within moments of stepping into the home that I visited with other media members from Canada, I was picturing returning with my son and his cousins or friends, and their parents. There is so much room and comfort that you could easily envision a group visit where all guests can retreat to their individual spaces when they want or need and return to the community features — games rooms, theatre, pool — to have fun together.

Of the 10 bedrooms, six feature king beds with private en suite baths. Kids’ rooms include one designed to look like a hot-air balloon with bunk beds and elevated steps for little feet to pitter-patter into the eye-catching decoration, and another has beds inside a retrofitted helicopter. It’s like spending a night in an aerospace-themed amusement park.

MORE: A Toddler’s First Visit to Disney

Canadians have increasingly gravitated toward the vacation-home option when visiting Florida. A report from SIAT Inbound Survey Monitor showed that 14% of Canadian air travellers who arrived in the Greater Orlando Area in 2023 stayed in a vacation home. Overall, 814,147 air passengers landed at Orlando International Airport from Canada in 2023. Osceola County is a beneficiary of a significant portion of that tourism business. In the first quarter of 2024, Canadians staying in vacation homes in Osceola County accounted for 54.2% of the total international guests and the average duration of their stay was eight days, according to Experience Kissimmee. KeyData estimates that the average revenue per guest is $2,797 USD (approximately $3,827 CAD).

The vacation home is a sensible transition from the theme parks, because it opens itineraries to include the area’s educational opportunities that can be a respite from the high-stimulation rides and character meetups. Parents will appreciate Kissimmee for the nature activities that provide a break — both financially and from the hectic pace — of the theme parks. Four excursions that I participated in during an April visit included:

1. Kayaking with the Paddling Center at Shingle Creek: Noted for being the closest place to Disney World for kayaking, Shingle Creek is a good spot for novice paddlers. Guide Ryan Hinton, 21, led our group of six, paired in double kayaks, through the shallow waters surrounded by cypress and pine trees. You may see alligators but Hinton and the outfitter company are adamant that the animals will not interfere with humans. I didn’t see one toothy reptile on the tour. Instead there were red-bellied turtles, a lonely benign snake on a branch, and a number of birds — cranes, blue herons, and hawks. The paddle is mostly easy, with the biggest risk being the likelihood of hitting sand and getting stuck in two feet of water. Navigating the tight passages between the trees is a unique challenge, especially for Canadians who are used to wide-open lakes. (Be mindful of your knuckles as you pass between trunks and branches.)
   

    

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   For the most part, it’s a serene trip that introduces families to the possibilities — and joys — of the region that aren’t nearly as heavily marketed. Cost: Self-guided, two-hour rentals cost $30 (all figures USD) for a single kayak or $50 for a tandem. Guided tours start at $59 for a single kayaker.

2. Boggy Creek Airboat Adventures: What started as a one-woman, one-boat tour operation has blossomed into an educational mainstay in Central Florida. The airboat tours are the anchor attraction. The rides last 30 minutes or one hour, and they bring you close to gators in the wild and zip you through marshy scenery with forever blue skies. That horizon would lull you to daydream if it weren’t for the excitement of the boat ride. Thanks to propellers on the back, the flat-bottomed airboat speeds across the top of the water, similar to how a float plane skims along before take-off. On shore, Boggy Creek also includes activities that will tickle kids’ curiosity. An enclosed butterfly garden has 17 different species of lepidoptera and five species of turtles; a mining activity allows kids to sluice for gems; and small gators, cared for by Gatorland, can be fed with sirloin biscuits purchased in the facility’s gift shop. There’s human food, too. Try the barbecue brisket, catfish po’boy sandwich, or gator bites (lightly breaded and tasty) at the on-site restaurant.
   

   An alligator in the wild nestles in the marsh as an airboat from Boggy Creek Adventures in Kissimmee passes by. (Adrian Brijbassi photo for Vacay.ca)

   “We love Canadians, and they love this park,” says Nick Romero, the attraction’s director of communications, noting that the plants and animals in the park are Indigenous to the state. “We’re here because we enjoy teaching people about the real Florida and we find our visitors from Canada, but also from Europe, appreciate that. They want to know more about the history and the environment here.”

   Cost: Airboat tours start at $32. Sunset and night tours are also available.

3. Reunion Resort and Golf Club: Located at the Magical Vacation Homes community in Reunion, the club features three courses, each designed by a golf great: Arnold Palmer, Jack Nicklaus, or Tom Watson. I played the Palmer course, which is loaded with bunkers and challenging water features.
   

   The Palmer course at Reunion Resort and Golf Club features holes that run alongside the backyard fences of vacation homes. (Adrian Brijbassi photo for Vacay.ca)

   As you play the course, you pass the Reunion community’s attractive homes — and hopefully avoid knocking a ball into one of the backyard pools. From the clubhouse, it was just an eight-minute walk back to the vacation home. Cost: $95 for green fees; $45 for rental clubs.

4. Earth Illuminated: A family-run immersive art experience that reimagines a future world, Earth Illuminated encourages participants to get playful with the exhibit space. There’s also a 10-course tasting menu available at Hidden Gems, the attraction’s speakeasy-style fine-dining restaurant with only 20 seats. Cost: Admission to Earth Illuminated is $18.86 with a 50% discount currently offered. Dinner at Hidden Gems costs $175 per person with an option for a $125 wine pairing per person.

Where to Dine in Kissimmee

Central Florida is known for its theatrics and that can extend to the dining scene, too. I indulged in a couple of notable places, such as:

Columbia: A starring restaurant with its roots in Tampa, Columbia blends Spanish and Cuban cuisine with delightful results. The signature chop salad, named “1905” for the year the first restaurant in Tampa’s Ybor City opened, is prepared tableside and tastes like a tart Caesar salad, thanks to the generous amount of Worcestershire sauce mixed in with bits of baked ham, and a blend of Swiss gruyère  and Romano cheese.

The paella is good for large groups, though it’s missing the traditional socarrat, the charred bottom, that is one of the hallmarks of the rice dish from Valencia. Overall, Columbia delivers excellent food with Old World service that’s worthy of theme-park status in itself. It’s located in Celebration, a picture-perfect community built by Disney.

JoJo’s ShakeBar: When it’s time for a treat — whether you’re a parent or a kid — JoJo’s is the place to go. Known for outrageous milkshakes, you can skip the salads and burgers, and go straight for the Three’s Company. It’s a strawberry-banana shake topped with chocolate-covered donut hole, chocolate cone, and sugar cookie. Or one of numerous similar concoctions that will challenge your sense of regret. Best part? I had no bellyache afterwards.

Themed on nostalgic U.S. diner life, the restaurant features arcade games, murals of pop icons from the ’80s and ’90s, and a TV behind the bar that shows “Grease” in its entirety.

JoJo’s is a national chain that started in Chicago and its first Florida location launched in March at Pointe Orlando, a lively plaza with multiple restaurants and entertainment venues.

Broadway Pizza Bar: No fancy food or entertainment at this staple on Kissimmee’s Main Street — just quality wood-fired pizza and other reasonably priced fare prepared by a multigenerational Italian family.

Where to Shop Near Disney

Orlando Vineland Premium Outlets: This spring, Dolce & Gabbana joins the luxury collection at the outlet centre close to Disney. The Milan-based fashion and home decor icon will be in good company at Florida’s largest outdoor mall. Gucci, Prada, Kate Spade, and other lux brands are already thriving at the outlet centre.

The mall’s retailers feature discounts on the previous year’s inventory as well as current offerings that would be overstocked in their primary locations. (A sister outlet mall with a smaller number of luxury retailers is near Orlando Universal Studios.)

MORE ABOUT VISITING KISSIMMEE

Getting There: Kissimmee, whose name means “long waters” in the language of the Indigenous Jororo peoples, is a short drive from Orlando International Airport. Canadians in Toronto and Calgary enjoy direct flights nearly every day to Orlando on Air Canada and Westjet; while Air Canada offers flights on most days from Montreal. There is one weekly Westjet flight from Vancouver to Orlando (and that number increases to twice a week from June 17 to September 1).

 

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Experience Kissimmee Accommodations: The tourism board works with more than 115 property rental companies. They include options like a mansion with 15 bedrooms and a newly opened three-storey, 12-bedroom giant built in the shape of a spaceship.

The homes are often also listed on popular sites like Airbnb and VRBO, but some may cost less if booked directly through the rental company. Find those listings when you search the Experience Kissimmee website.

“Post-pandemic, Kissimmee has seen an influx of visitors, leading to a strong surge in accommodation bookings. Kissimmee experienced an overall 62% rebound in 2022, effectively returning to pre-pandemic levels compared to those in 2019. Additionally, there was an 8% uptick in vacation home bookings,” says Juliana Leveroni, director of communications for Experience Kissimmee.

Disclosure: Experience Kissimmee facilitated the visit by Vacay.ca Managing Editor Adrian Brijbassi with travel, accommodations, dining, and attraction costs. No business or organization reviewed the article before it was published.