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Holiday rentals in Kissimmee

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Top-rated holiday rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Apartment in Kissimmee
Minutes To Disney World - Sparkling Clean Condo
Super clean newly renovated condo in Kissimmee, FL 🚗 15 minute drive to Walt Disney World 🚗 25 minute trip to Universal Studios 👮‍♀️Gated community with 24/7 security on site. 👨‍🍳 Full kitchen with everything you need 🧺 Washer/dryer in unit 💻 Fast wi-fi and smart tv's with access to netflix/hulu and cable. 🏊‍♂️ Zero entry heated swimming pool 💪🏼 Full Gym, basketball, tennis courts and walking trails. 🥇Airbnb Superhost We would love to have you stay! Book this Orlando condo Today!
2–9 DecIndividual Host,
£109 per night
4.91 out of 5 average rating, 203 reviews
Guest favourite
Guest suite in Kissimmee
Newly renovated near Disney and Universal Orlando
Entire suite , new ultra comfortable king size bed, free wifi, 64"TV with Netflix and Amazon Prime. Private bath, Living room and kitchen, shared laundry room, free parking 13 miles or 21 minutes from Disney World, Disney Springs shops and restaurants and Orlando Premium Outlets 16.6 miles or 23 minutes from Universal Orlando. 12.6 miles or 22 minutes from Aquatica and SeaWorld Orlando 11.6 miles or 22 minutes from Orlando International Airport 15 miles or 25 minutes from the Convention Center
4–11 JanIndividual Host,
£71 per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Home in Kissimmee
Upscale Contemporary Waterfront 3/2 Heated Pool
Right on water, private freestanding house,screened in pool,close to all attractions, airport.This house is one of a kind,contemporary renovated in European style,full of palm trees,quiet neighborhood,new AC and appliances. Spectacular fireworks:New Year,4th of July over the lake.Enjoy beautiful sunsets every evening at the pool area and listen to your favorite music with Alexa echo dot!Self check in process.Best location!We are close to Disney, Universal,Cocoa beach.Heated pool extra $25/day.
26 Jun – 3 JulIndividual Host,
£256 per night
4.97 out of 5 average rating, 259 reviews

Popular amenities for Kissimmee holiday rentals

Stay near Kissimmee's top sights

Medieval Times Dinner & Tournament346 locals recommend
Silver Spurs Arena9 locals recommend
FantasyWorld Resort7 locals recommend
Give Kids The World Village7 locals recommend
Osceola Heritage Park12 locals recommend
Walmart Supercenter44 locals recommend

Other great holiday rentals in Kissimmee

Guest favourite
Tiny home in Kissimmee
Blue Bungalow Tiny House near all Attractions!!
8–15 SeptProfessional Host,
£93 per night
4.95 out of 5 average rating, 323 reviews
Guest favourite
Guest suite in Orlando
Location, Location, Location near all attractions
7–14 SeptIndividual Host,
£138 per night
4.99 out of 5 average rating, 238 reviews
Guest favourite
Townhouse in Kissimmee
Resort-style home close to Disney with jacuzzi
26 Jan – 2 FebProfessional Host,
£148 per night
4.97 out of 5 average rating, 170 reviews
Guest favourite
Guest house in Kissimmee
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
21–28 FebIndividual Host,
£97 per night
4.89 out of 5 average rating, 84 reviews
Superhost
Cabin in Kissimmee
Romantic Cabin w/ Balcony + Tub + Hammock + Grill
14–21 OctIndividual Host,
£176 per night
4.81 out of 5 average rating, 27 reviews
Guest favourite
Flat in Kissimmee
It's too much like a elegant mini-hotel (6)
7–12 JulIndividual Host,
£52 per night
5.0 out of 5 average rating, 19 reviews
Guest favourite
Tiny home in Kissimmee
Luxury Tiny Cottage. Only 5 miles from Disney!
29 Aug – 5 SeptIndividual Host,
£95 per night
4.98 out of 5 average rating, 40 reviews
Guest favourite
Apartment in Kissimmee
Fabulous location in the world of Disney
12–19 OctProfessional Host,
£98 per night
4.93 out of 5 average rating, 14 reviews
Superhost
Guest suite in Orlando
Beautiful Suite, with independent entrance parking
6–13 FebIndividual Host,
£61 per night
4.81 out of 5 average rating, 27 reviews
Guest favourite
Guest house in Orlando
Guesthouse hosted by Yadier
23–30 MayIndividual Host,
£109 per night
5.0 out of 5 average rating, 44 reviews
Guest favourite
Place to stay in Kissimmee
Temple+A/C Glamping+Hot Tub, near MCO/PARKS
14–21 MayIndividual Host,
£170 per night
4.94 out of 5 average rating, 89 reviews
Guest favourite
Home in Kissimmee
Tranquil Private Villa * Minutes From Disney
24–31 AugIndividual Host,
£113 per night
4.89 out of 5 average rating, 27 reviews

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

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  4. Osceola County
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