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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.

Superhost
Apartment in Kissimmee
54A DISNEY-STAR ISLAND-1 BR SLP 4-TENNIS/POOLS/SPA
An Orlando Adventure with All the Extras. Parking & resort fees included. Star Island, a 5 star resort located Just 10 minutes from Walt Disney World® in popular Kissimmee. It offers so many fun on-site amenities & activities, it actually rivals the magic of Orlando itself. Enjoy the resort at a fraction of the parks. amenities : 2 pools, SPA's, Fitness center, Golf-Driving range, Tennis and Basketball Courts, Pickle Ball courts, Volleyball courts, Water sports, Pool Bar, Ping Pong, Game Room
Individual Host
Superhost
Guest suite in Kissimmee
Fully independent guest suite
Relax in this quiet, sleek space. Located in Kissemee, it is a cozy and comfortable space for spend a few unforgettable days of vacation. Our private space has a spacious bedroom and it has a bed in the, bathroom,kitchen and a large patio where you can share with your friends and loved ones. Guests have free access. This is also close to major Disney parks and other Orlando attractions.
Individual Host
Superhost
Loft in Orlando
UPSCALE LOFT SPACE CLOSE TO DOWNTOWN.
Conveniently located between Downtown’s Lake Eola and the foodie-friendly Milk District, this beautifully unique space features an open floor plan with floor to ceiling windows allowing natural light to fill the space. You’re only a short drive to upscale Winter Park restaurants and the vibrant Thornton Park art scene.
Individual Host

Stay near Kissimmee's top sights

Medieval Times Dinner & Tournament347 locals recommend
Walmart Supercenter44 locals recommend
Silver Spurs Arena9 locals recommend
FantasyWorld Resort7 locals recommend
Give Kids The World Village7 locals recommend
Osceola Heritage Park12 locals recommend

Other great holiday rentals in Kissimmee

Superhost
Tiny home in Kissimmee
Small Cottage - clean, cozy and safe
Professional Host
Superhost
Loft in Orlando
Contemporary Loft Near Downtown
Individual Host
Superhost
Hotel room in Orlando
PentHouse Suite with 2X View
Individual Host
Superhost
Apartment in Kissimmee
Amazing ❤️ Water View Condo near Disney & Universal
Individual Host
Superhost
Apartment in Orlando
Discounted - Deluxe Studio:Lakeview, parking, pool
Professional Host
Superhost
Townhouse in Davenport
No Airbnb Fees! Private Pool in Resort /Clubhouse.
Professional Host
Superhost
Apartment in Kissimmee
Amazing Resort Condo Near Disney.
Professional Host
Superhost
Guest suite in Orlando
Elegant home & Oasis mood centrally located & pool
Individual Host
Superhost
Flat in Davenport
Modern Resort 1BDApt near Disney
Individual Host
Superhost
Townhouse in Kissimmee
Modern & Cozy Townhome at Storey Lake
Professional Host
Superhost
Apartment in Orlando
Wyndham Bonnet Creek ツ 1 Bedroom Deluxe!
Professional Host
Superhost
Flat in Kissimmee
Boho Style Studio Apartment
Individual Host

Quick stats about holiday rentals in Kissimmee

Total rentals

7.2K properties

Rentals with dedicated workspaces

3.6K properties have a dedicated workspace

Rentals with a pool

6.4K properties have a pool

Pet-friendly rentals

1K properties allow pets

Family-friendly rentals

6.2K properties are a good fit for families

Total number of reviews

187K 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

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee