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Holiday rentals in Kissimmee

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Kissimmee

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

Superhost
Tiny home in Kissimmee
Small Cottage - clean, cozy and safe
Cozy cottage located only 4 MILES TO DISNEY WORLD!!! The cottage is so close to everything yet surrounded by lush trees, established landscaping and an ever so peaceful setting. 0.2 miles to ALDI. 2 miles to Wal-Mart. 7 miles to Sea World. 8 miles to Orange County Convention Center. 12 miles to Central Florida Fairgrounds. 13 miles to Universal Studios. 14 miles to Premium Outlet. 17 miles to MCO airport.
$94 SGD per night
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 on vacation. Our private space has a spacious bedroom and has a bed in the bathroom, bathroom,kitchen and kitchen large patio where you can share with your friends and loved ones. Guests have access free. This one is also close to major Disney parks and other Orlando attractions.
$69 SGD per night
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.
$170 SGD per night

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
Loft in Orlando
Contemporary Loft Near Downtown
$150 SGD per night
Superhost
Apartment in Kissimmee
54A DISNEY-STAR ISLAND-1 BR SLP 4-TENNIS/POOLS/SPA
$235 SGD per night
Superhost
Hotel room in Orlando
PentHouse Suite with 2X View
$294 SGD per night
Superhost
Flat in Orlando
Calena Romantic, Contemporary Studio W/Terrace ❤️❤️
$137 SGD per night
Superhost
Townhouse in Davenport
No Airbnb Fees! Private Pool in Resort /Clubhouse.
$234 SGD per night
Superhost
Apartment in Kissimmee
Amazing Resort Condo Near Disney.
$163 SGD per night
Superhost
Apartment in Orlando
Last minute discount - Studio close to Universal
$114 SGD per night
Superhost
Flat in Davenport
Modern Resort 1BDApt near Disney
$150 SGD per night
Superhost
Townhouse in Kissimmee
Modern & Cozy Townhome at Storey Lake
$280 SGD per night
Superhost
Apartment in Orlando
Wyndham Bonnet Creek ツ 1 Bedroom Deluxe!
$160 SGD per night
Superhost
Flat in Kissimmee
Boho Style Studio Apartment
$86 SGD per night
Superhost
Flat in Kissimmee
Comfortable Apartment in Kissimmee
$86 SGD per night

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

Destinations to explore

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