
Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Other great holiday rentals in Kissimmee

Solterra discount slps 18/7 bdm/GR/pool/spa5485
The house is brilliant. We had 11 adults and a 5 month old baby. We all flew in at different times, to different airports but access was easy for everyone. we had been given the details by the host prior to our arrival. Susan is a great host, very communicative but not intrusive. Every detail was taken care of. Passes at the gate, information about the activities and much more. I would highly recommend this AirBnB to anyone. Having a large family, it was great for space but also playing games and spending time together. We had family visit, who live in Florida, which was also easy. Susan was very helpful when my father in law couldnt be located, after visiting us. Thank you Susan, we will be back

Cute Vacation Home Very Close to Disney
We really enjoyed the house and pool. It was very convenient to parks and shopping /restaurants.

The great Florida escape!
The place was perfect for our family and well equipped for our two little ones aged 3 and 9 months. Daniel was quick to communicate when we had questions.

Dream vacation, near Disney
What an incredible stay we had at Rosario's place! We even extended 2 extra nights. Rosario was responsive, helpful, and so kind - she even left a birthday balloon and some treats for my mom's birthday! The house was impeccable and they were great about everything, from changing dates to heating the pool, and keeping it clean, and the pool was a perfect balmy respite. The next time we're in town (and we will be, this is our old neighborhood!), we will definitely try to book here again. Can't wait to come back!

New! Windsor Island Resort with pool by Disney 03
Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.

Pelican Escape
Our stay was very comfortable. Not far from Disney and other attractions. My family had everything they needed, would stay again in the future!

DisneyVacationHomeLazyRiver9021
This beautiful home worked well for our family…4 couples and 3 small children. Pool and hot tub were great and clean! The house was large and we had a ton of fun! The host was super responsive every time we sent a message. We would definitely come back to this house and would highly recommend it!

Disney, Villa Runaway Beach, Kissimmee 2
Monica and Sebastian have a beautiful place, home feeling and absolutely beautiful. Getting into the place was easy and getting in the home was very easy too. We were very happy with our stay. The apparent is cozy and the apartment complex is very beautiful and super clean. We enjoyed our stay. Thank you Brenda and Manny
Quick stats about holiday rentals in Kissimmee
Total rentals
7.2K properties
Total number of reviews
242K reviews
Family-friendly rentals
6.1K properties are a good fit for families
Pet-friendly rentals
1.1K properties allow pets
Rentals with a pool
6.5K properties have a pool
Rentals with dedicated workspaces
3.9K properties have a dedicated workspace
Your guide to Kissimmee
All about Kissimmee
Located in the middle of central Florida, Kissimmee is perfectly positioned to give you access to the best of the region, including the world-famous theme parks and waterparks in nearby Orlando; vast, mirrored tracts of swampland; thousands of deep green lakes and springs; or some of Florida’s famous citrus groves. You can even get to popular coastal spots like Cocoa Beach and Daytona from Kissimmee in under two hours. The town exudes welcoming, small-town charm. There are no skyscrapers here, and almost 200 buildings in the downtown area are on the National Register of Historic Places. There’s plenty of outdoor recreation inside the city limits too, at Shingle Creek Regional Park, where visitors can hike and kayak.
The best time to stay in a holiday rental in Kissimmee
The weather in central Florida is nice year-round — there’s a reason it’s called the Sunshine State. Winters in Kissimmee tend to be sunny, warm, and dry, so around the holidays, Florida tends to be a popular escape for those who live in colder climates. Though temperatures hover around 70 degrees Fahrenheit from December through February, you’ll still want to pack a jacket. In the busy summer months, you can expect temperatures around 90 degrees and the kind of humidity that makes air conditioning a necessity. Keep in mind that summer and early autumn also bring hurricanes to Florida. Spring and fall can be considered the best of both worlds, with lovely weather and fewer crowds, ideal seasons to stay in one of the area’s villas.
Top things to do in Kissimmee
Old Town
Crowned with a candy-colored Ferris wheel, Kissimmee’s Old Town outdoor shopping and entertainment complex is a re-creation of a turn-of-the-century Florida town. The brickwork pedestrian streets are lined with boutiques, restaurants, amusement rides, and arcades with new and classic games, including laser tag. Be sure to catch weekly events such as the classic car parades and the outdoor Family Movie Night.
Fan Boat Swamp Tour
Shingle Creek, which runs right through the city of Kissimmee, is widely considered the headwaters of Florida’s famous Everglades. While Everglades National Park is a few hours away in South Florida, you can head to one of the lakes around Kissimmee on a fan boat tour to experience the same wetland environment, where you’ll spot water birds, deer, wild pigs, and alligators.
Hot Air Balloon Ride
Get a whole new perspective on Central Florida’s best-known attractions on a sunrise hot air balloon ride. You could float above a theme park, still quiet before it opens to the public; dip down over one of the region’s many freshwater lakes and springs; or catch whiffs of the orange trees’ perfume when they’re in bloom.
Destinations to explore
- Four Corners Holiday rentals
- Orlando Holiday rentals
- Central Florida Holiday rentals
- Saint Johns River Holiday rentals
- Tampa Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- Cocoa Beach Pier
- ESPN Wide World of Sports
- Universal Orlando Resort
- Reunion West
- Amway Center
- Kissimmee Lakefront Park
- ChampionsGate Golf Club
- Epcot
- Disney's Hollywood Studios
- Universal's Islands of Adventure
- Blue Spring State Park
- Magic Kingdom Park
- Aquatica
- ICON Park
- Island H2O Water Park
- Things to do Kissimmee
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- Things to do Osceola County
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