Kissimmee is often mistaken for a neighborhood in Orlando. In fact, it is a city in Osceola County, Florida. It is part of the so-called Greater Orlando (Orlando metropolitan region) and is one of the most sought-after regions for vacation rentals by tourists, as it is very close to Disney parks and home to several Vacation Home condominiums. In addition to the parks, the city and its surroundings offer several attractions in the middle of nature and also culturally rich tours.
The city is also one of the most sought-after destinations by global investors looking for high returns on vacation rentals. Because it has clear and objective legislation on vacation rental rules, the city stands out from other regions in Florida, providing security for this type of investment.
In this article, we will discuss the city’s main attractions, the Vacation Home market and also relevant information for those thinking of living in Kissimmee.
Things to do in Kissimmee! Must-See Attractions
Kissimmee offers a variety of attractions and entertainment options for all tastes. From world-class theme parks and outdoor activities to restaurants and shopping venues, the city has plenty to explore. Below, we highlight some must-visit attractions, activities, and shopping spots in the area.
1 – Enjoy some of the bet theme parks in Orlando
Kissimmee is one of the most strategically located areas in terms of proximity to Central Florida’s major theme parks. This has made the city a highly sought-after destination for tourists, whether for stays in hotels or in vacation homes.
Just a few minutes’ drive away, visitors can easily access the Walt Disney World Resort parks, including Magic Kingdom, Epcot, Disney’s Hollywood Studios, and Animal Kingdom. Beyond Disney, Kissimmee is also close to the Universal Orlando Resort, which features Universal Studios Florida and Islands of Adventure, and the SeaWorld Orlando complex, known for its thematic attractions and marine life encounters.
Within the city itself, Kissimmee offers attractions like Gatorland, an iconic park featuring alligator exhibits and educational experiences about local wildlife. Another notable option is Fun Spot America, an amusement park with roller coasters, go-kart tracks, and family-friendly games, providing an exciting and accessible experience for all ages. This combination of attractions and convenience makes Kissimmee a comprehensive and appealing destination for both tourists and real estate investors.
2 – Old Town Kissimmee
Old Town is definitely an attraction that should be on your list of things to do in Kissimmee!!
Old Town Kissimmee is a charming shopping and entertainment center that feels like stepping into a vintage village with a nostalgic atmosphere. Situated on US 192 and just minutes from major attractions like Walt Disney World Resort and Universal Orlando, Old Town spans 18 acres and is filled with over 70 locally-owned shops, restaurants, bars, and unique attractions. This historic district preserves classic architecture and distinctive storefronts, inviting visitors to take a leisurely walk and soak in the relaxed, old-time Florida ambiance.
The attractions at Old Town cater to all ages, offering a blend of fun and tradition. Visitors can explore Mortem Manor, an acclaimed haunted house, or enjoy the views from the 86-foot Ferris wheel. The weekend classic car show is a highlight, where vintage cars are displayed and celebrated with a parade that has been running for over three decades. This event, along with live entertainment at the Trophy Row Stage, creates a lively atmosphere that embodies the spirit of community and the joy of simpler times.
Adjacent to Old Town is the popular Celebration Suites hotel, known for its fair pricing and excellent location, making it a favorite among tourists.
5 – Celebration Community
The Celebration community in Kissimmee is mistaken by many tourists as a neighborhood or a large luxury condominium. In fact, it is a bit of all of these. Celebration is a planned community, based on Walt Disney’s model city ideals. Everything is very well thought out, beautiful and within a strict standard of maintenance and aesthetics. It looks like a movie set. Celebrities have very expensive homes in the region. It is worth strolling through downtown Celebration and having lunch or dinner at one of the great restaurants. It’s a great place to relax and get away from the hustle and bustle of the parks. Learn more about Celebration Orlando.
6 – Extreme and outdoor activities
Kissimmee also offers a number of parks for more extreme and outdoor activities. Take advantage of boating, canoeing, kayaking, zip-lining, and other activities.
For those who don’t know, around the theme parks there are several forests and lots of untouched and preserved nature, rich in biodiversity. Kissimmee offers a number of sports and outdoor activities to enjoy this exuberant nature of central Florida. One of them is to visit The Paddling Center. This is a nature center where you can rent kayaks, canoes, StandUp Paddles, bicycles or even walk within the complex on the various trails through the forests. Everything is very safe and organized. Learn more about the nature attractions offered by The Paddling Center.
7 – Shopping at The Loop shopping center in Kissimmee
The Loop is one of the best shopping centers in Kissimmee. If you enjoy shopping, you shouldn’t miss it. It’s like an open-air mall, divided into two zones: 1 – The Loop and 2 – The Loop West. Both are separated by a street. These open-air shopping centers offer a variety of shops, restaurants and entertainment.
The Loop is not as complete as the large and famous outlets in Orlando, but it is very popular especially for those who don’t want crowded stores and long lines. The stores are well spread out and open-air. The prices are equally good when compared to the other outlets in Orlando.
Click here to visit the resort’s official website for more information
8 – Natural beauty and outdoor activities in Kissimmee
Kissimmee is surrounded by natural beauty and offers a wide variety of outdoor activities for visitors to enjoy. One of the main highlights is Lakefront Park, a vast park filled with trees where families can walk, picnic, sunbathe, fish, and even enjoy a barbecue with friends. The park also boasts a great playground for children, kayak rentals, boat tours, and a fishing pier, making it a perfect spot for relaxation and recreation.
For those interested in conservation and wildlife, the Disney Wilderness Preserve is a must-visit. Spanning 11,000 acres, this area is home to diverse native plants and animals and offers hiking trails for exploration and birdwatching, all while showcasing local conservation efforts supported by the Walt Disney Company. For an adventurous twist, visitors can experience Boggy Creek Airboat Rides, gliding through the swamp to spot alligators, turtles, and various waterfowl.
Kissimmee is also part of the Kissimmee Chain of Lakes, a series of interconnected lakes. Living near these lakes offers residents the chance to engage in activities such as boating, fishing, and watersports, creating a unique connection to the natural environment.
And more..
There are other tours and things to do in Kissimmee. We have listed the main ones above. You can also take a hot air balloon ride, ride a helicopter or even visit other parks in the region that offer outdoor activities or extreme rides.
The lucrative Vacation Home market
Kissimmee is often regarded as the ‘mecca’ of Vacation Home communities. Its proximity to the theme parks and flexible rental regulations have turned the city into one of the top global destinations for Vacation Home investment.
The city attracts over 70 million visitors annually, virtually ensuring an excellent occupancy rate for those aiming to profit from short-term rentals.
For this reason, investing in vacation homes in Orlando is currently one of the best real estate deals in the world.
Vacation homes in Orlando are becoming increasingly popular compared to hotels, offering a range of advantages for visitors. These homes are spacious, with many featuring private pools, barbecue areas, game rooms, home theaters, and other amenities that elevate the guest experience. Often decorated with themed designs, they create a magical atmosphere, especially for children. For those traveling in groups, the connections formed with friends and family in these homes make the stay far more enjoyable than in a hotel.
Staying in a vacation home also provides a genuine experience of what it’s like to live in Florida. Guests can shop at local supermarkets and prepare their own meals, which makes the stay not only more affordable but also healthier. These are just some of the benefits that set vacation homes apart from hotels. For these reasons and more, vacation homes have become one of the most attractive real estate investments for global investors.
Many of our clients have purchased a vacation home and were so pleased with their investment that they went on to buy a second, a third, and more. It’s not uncommon to find individuals owning more than four homes spread across the top communities in Orlando. Essentially, they become owners of a small hotel network, as this has evolved into a lucrative business model. One of the biggest advantages is leveraging the investment through bank financing and using the rental income generated by the property itself, thus multiplying their assets.
Living in Kissimmee: What You Need to Know
Kissimmee’s proximity to Disney parks, shopping centers, natural parks, and various attractions makes it an attractive choice for buying a home to live or investing. Howerver, it’s crucial to be cautious about the location.
Given the city’s popularity as a tourist destination, it’s recommended to look for more residential neighborhoods that provide a peaceful environment, away from the intense flow of visitors. Choosing such areas can ensure a higher quality of life and greater privacy for residents.
A frequently asked question from our real estate clients is whether it’s feasible to live in Kissimmee’s Vacation Home communities.
While many enjoy short stays in these communities and appreciate the quality of life they offer, they might not be ideal for permanent living.
The main reason is the high turnover of tourists in these areas. Living on a street where neighbors change weekly may not provide a stable sense of community. Forming lasting friendships with neighbors can be difficult, which is especially challenging for families with children, as the neighbors you see today may be gone by the following week.
Additionally, many of these communities have rules that limit the maximum length of stay.
For a more residential atmosphere, Kissimmee has neighborhoods like Celebration and Hunters Creek. Beyond Kissimmee, other nearby cities such as Winter Garden, Windermere, and Winter Park provide quieter, family-friendly environments, excellent schools, and a high quality of life.
Before choosing where to live in Kissimmee, consult an experienced real estate agent and consider factors like school quality, safety, and proximity to work and attractions.
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