Holiday rentals in Kissimmee
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Top-rated holiday rentals in Kissimmee
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Cottage in Kissimmee
4.98 out of 5 average rating, 134 reviewsRunaway Beach Club Private Patio:Disney, Universal
Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.
11–18 Sept
Home in Winter Garden
4.92 out of 5 average rating, 164 reviewsCozy Winter Garden Home 20 MINUTES FROM DISNEY
Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.
18–25 Nov
Flat in Kissimmee
4.92 out of 5 average rating, 200 reviewsModern APT W/ Patio 15 mins from Theme Parks & MCO
Beautiful space where you can spend a beautiful vacation with your loved ones, the space is created with immense love and for you to feel at home. El acceso será autónomo, con llavín inteligente y una entrada completamente independiente y sin restricción de horario . Ofrecemos un patio exterior diseñado para tiempo de descanso,para compartir un café y también para fumar si fuera de su agrado El parqueo está concebido para dos autos y tenemos cámara de seguridad las24h Todo climatizado
6–13 Jun
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee holiday rentals
Other great holiday rentals in Kissimmee
Apartment in Kissimmee
4.98 out of 5 average rating, 283 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
22–29 Aug
Home in Kissimmee
4.84 out of 5 average rating, 204 reviews3 bedroom Villa in Kissimmee
23–30 Sept
Apartment in Kissimmee
4.91 out of 5 average rating, 111 reviewsFirst floor/your Disney escape
18–25 Sept
Cottage in Kissimmee
4.94 out of 5 average rating, 364 reviewsEntire Cottage close to Disney, Universal, Airport
11–18 Jun
Tiny home in Kissimmee
4.9 out of 5 average rating, 433 reviewsZMZ Tiny House Living! Try it out while at Disney
18–25 Sept
Holiday home in Orlando
4.82 out of 5 average rating, 100 reviewsThe Lovers Haven (Romantic Studio w/ Balcony)
12–19 Sept
Guest house in Kissimmee
4.93 out of 5 average rating, 135 reviewsStylish guesthouse close to Disney
2–9 Jul
Tiny home in Kissimmee
4.95 out of 5 average rating, 142 reviewsDisney Tiny House Getaway!
29 Apr – 6 May
Apartment in Kissimmee
4.88 out of 5 average rating, 48 reviewsStylish Condo 20 mins to Disney/King Bed
26 Sept – 3 Oct
Townhouse in Kissimmee
5.0 out of 5 average rating, 9 reviewsSummer Studio at Kissimmee
12–19 Sept
Guest house in Orlando
5.0 out of 5 average rating, 44 reviewsGuesthouse hosted by Yadier
29 May – 5 Jun
Apartment in Kissimmee
5.0 out of 5 average rating, 7 reviewsResort Oasis Near Disney World
29 Sept – 6 Oct
Quick stats about holiday rentals in Kissimmee
Total rentals | 7.6K properties |
---|---|
Rentals with dedicated workspaces | 3.9K properties have a dedicated workspace |
Rentals with a pool | 6.8K properties have a pool |
Pet-friendly rentals | 1.1K properties allow pets |
Family-friendly rentals | 6.6K properties are a good fit for families |
Total number of reviews | 197K reviews |
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
- St Petersburg Holiday rentals
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