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We found 22,568 holiday rentals — enter your dates for availability
Discover a selection of more than 10,000 holiday rentals in Kissimmee, FL, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including private pool and pool. Prices start at £ 95 per night, and villas and houses are popular options for a stay in Kissimmee. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Kissimmee
Top rated rentals — Kissimmee
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Destination guide
Enjoy amusement parks and adventures from Kissimmee villas
Another popular central Florida holiday destination is Kissimmee. Florida villa rentals are abundant in Kissimmee, and this is a top spot for golf and family fun. Kissimmee is in an ideal location to enjoy the amusement parks and adventures that are available in Orlando. The proximity to Orlando also means you'll likely find top-notch villas for a great price. Kissimmee has plenty of amazing attractions in its own right as well, such as swamp tours to see Florida wildlife up close and Old Town Kissimmee with its world-class shopping and dining. Kissimmee is also lovely for a romantic getaway.
Activities
Sightseeing in and around Kissimmee
Are you hoping to find things to do while you're in the area? Venture out of your holiday home and experience everything that makes Kissimmee a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:
- SeaWorld® Orlando (8.9 mi / 14.3 km)
- Universal Studios Florida™ (12.8 mi / 20.5 km)
- Walt Disney World® (13.6 mi / 21.9 km)
- Gatorland® (3.8 mi / 6.2 km)
- Discovery Cove (8.4 mi / 13.6 km)
- Aquatica (8.9 mi / 14.3 km)
Weather
Seasonal weather averages in Kissimmee
If you're hoping to enjoy some warm-weather activities on your holiday, July, August, June and September are the hottest months to visit, when temperatures average 33°F.
Natural features
Exploring the natural landscape of Kissimmee
Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Kissimmee is a great place to get outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:
- Kissimmee Lakefront Park (0.2 mi / 0.4 km)
- Brinson Park (0.5 mi / 0.8 km)
- Shingle Creek Regional Park (3 mi / 4.8 km)
- Lake Cecile (5 mi / 8 km)
- Lake Tohopekaliga (6.2 mi / 10 km)
- Lake Bryan (7.5 mi / 12.1 km)
How to get there
Transport to and around Kissimmee
The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 1.9 mi (3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Orlando, FL (MCO-Orlando Intl.), which is 11.2 mi (18 km) away.
If you're travelling by train, the main station serving the city is Kissimmee Station.
How to get around
Getting around holiday rentals in Kissimmee
Rental cars are ubiquitous in Kissimmee and a vast majority of the travellers who head here on a family break will opt for their own wheels. It's easy to see why. Not only do loads of Kissimmee holiday homes come with on-site parking but the city is really well-linked to Highway 192. That has 2 advantages; 1st, it connects with Interstate 4 to get you to the theme parks in less than 30 minutes, and 2nd, it connects with Route 441, to get you to Orlando International Airport in just 25 minutes. There is a public bus provider for those determined not to rent a car. It's called the LYNX network and has routes going to central Orlando and the popular draws along International Drive.
Restaurants and bars
Restaurant areas to try near Kissimmee holiday homes
- Historic Downtown Kissimmee is the main place to dine, with its fun-loving themed restaurants
- Lake Buena Vista is home to more family eateries than you can shake an American burger at – go there for dining close to Disney World
- Budget buffet restaurants can be found fringing the edges of Highway 192
- Head up to Hollywood Way to find rock-themed cocktail bars, sushi kitchens and Cajun shrimp cooks
- This whole area of central Florida is a great place to be if you like Tex-Mex food and BBQ – try Main Street and Vine Street for those
Essential info
Kissimmee facts to know for travellers
- Kissimmee has a population of just under 70,000
- Kissimmee is often coupled with the nearby town of St Cloud, called the Kissimmee-St Cloud area
- The closest major airport is the huge Orlando International Airport
- The hurricane season lasts from June to November, so be ready for some storms in Kissimmee then
- Kissimmee holiday rentals tend to be popular at Christmas and during major holidays
Family friendly
Fun for the whole family in Kissimmee
Kissimmee villa rentals are a real family favourite. That's not just because they often come with on-site pools and plenty of bedrooms, but also because they sit right on the cusp of some of the Sunshine State's most fun-inducing draws. Walt Disney World is the obvious chart-topper. It sprawls out, with its clutch of different theme parks, just a whisker to the north-west – home to the mighty Animal Kingdom and the spires of Cinderella's castle. Universal Studios is also up that way, packed with Harry Potter-themed attractions and cartoon-inspired roller coasters. Closer to home, you can hit the Osceola Heritage Park for days of Major League Baseball showdowns, or sample Silver Spurs Arena for rollicking rodeos at night.
How many holiday rentals are available around Kissimmee?
Our 2021 accommodation listings offer a large selection of 22,568 holiday lettings around Kissimmee. From 5,431 villas to 17,644 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.
Can I rent Villas in Kissimmee?
Yes, of course. Vrbo UK offers 5,431 Villas in Kissimmee. Our other popular types of Kissimmee holiday rentals include:
- Houses: 17,644 self catering accommodations
- Resorts: 972 self catering accommodations
- Flats: 3,484 self catering accommodations
But you can also enjoy a great stay in one of our other holiday rentals including Bungalows and more.
Can I find a holiday accommodation with pool in Kissimmee?
Yes, you can select your preferred holiday accommodation with pool among our 20,915 holiday homes with pool available in Kissimmee. Please use our search bar to access the selection of holiday rentals available.