Some info has been automatically translated. Show original language

Vacation rentals in Kissimmee

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kissimmee

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

Guest favourite
Condo 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!
Dec. 2 – 9
$187 CAD 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
Jan. 4 – 11
$122 CAD 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.
Jun. 26 – Jul. 3
$440 CAD per night
4.97 out of 5 average rating, 259 reviews

Popular amenities for Kissimmee vacation 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 vacation rentals in Kissimmee

Guest favourite
Tiny homes in Kissimmee
Blue Bungalow Tiny House near all Attractions!!
Sep. 8 – 15
$160 CAD per night
4.95 out of 5 average rating, 323 reviews
Guest favourite
Guest suite in Orlando
Location, Location, Location near all attractions
Sep. 7 – 14
$238 CAD per night
4.99 out of 5 average rating, 238 reviews
Guest favourite
Townhouse in Kissimmee
Resort-style home close to Disney with jacuzzi
Jan. 26 – Feb. 2
$256 CAD per night
4.97 out of 5 average rating, 170 reviews
Guest favourite
Guesthouse in Kissimmee
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Feb. 21 – 28
$167 CAD per night
4.89 out of 5 average rating, 84 reviews
Superhost
Cabin in Kissimmee
Romantic Cabin w/ Balcony + Tub + Hammock + Grill
Oct. 14 – 21
$289 CAD per night
4.81 out of 5 average rating, 27 reviews
Guest favourite
Apartment in Kissimmee
It's too much like a elegant mini-hotel (6)
Jul. 7 – 12
$88 CAD per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Tiny homes in Kissimmee
Luxury Tiny Cottage. Only 5 miles from Disney!
Aug. 29 – Sep. 5
$164 CAD per night
4.98 out of 5 average rating, 40 reviews
Guest favourite
Condo in Kissimmee
Fabulous location in the world of Disney
Oct. 12 – 19
$169 CAD per night
4.93 out of 5 average rating, 14 reviews
Superhost
Guest suite in Orlando
Beautiful Suite, with independent entrance parking
Feb. 6 – 13
$105 CAD per night
4.81 out of 5 average rating, 27 reviews
Guest favourite
Guesthouse in Orlando
Guesthouse hosted by Yadier
May 23 – 30
$187 CAD 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
May 14 – 21
$292 CAD per night
4.94 out of 5 average rating, 89 reviews
Guest favourite
Home in Kissimmee
Tranquil Private Villa * Minutes From Disney
Aug. 24 – 31
$194 CAD per night
4.89 out of 5 average rating, 27 reviews

Quick stats about vacation 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

Welcome to Kissimmee

Located in central Florida, Kissimmee is well situated near some of the most sought-after attractions in the state. Being so close to the Walt Disney World Resort, Universal Orlando Resort, and LEGOLAND Florida parks ensures that this city is popular with families and theme-park fans alike. Kissimmee has its own set of charms to entice visitors, including easy access to the Florida Everglades, the Kennedy Space Center, and many aquatic attractions. You can spend jam-packed days enjoying the company of fairy-tale creatures and riding thrill rides, then change it up with visits to the natural world and dreams of reaching for the stars in outer space. The city has its share of nationally known dining options to cater to visitors from around the world, including entertainment districts that combine the best in food, shopping, and fun. Whether you’re looking for magical lands, family fun, or a wide variety of entertainment options, Kissimmee will deliver an unforgettable holiday experience.


The best time to stay in a vacation rental in Kissimmee

Kissimmee’s busy season runs from March to August, with peak visitation periods taking place during U.S. Thanksgiving, Christmas, and Spring Break (generally March and April). During these times, Orlando’s theme parks are teeming with fans of every age, and the state’s heat and humidity are at their peak. To avoid the worst of the heat, consider booking one of the area’s vacation rentals for between October and March, when temperatures are a bit milder and the crowds have eased up slightly. Pack a light jacket or sweater to wear after the sun sets. The months of July through September are the rainy season in central Florida. Temperatures can often rise above 30 degrees Celsius, and afternoon thundershowers are a common occurrence, so be sure to have protective gear on hand.


Top things to do in Kissimmee

Immerse Yourself in Magical Worlds

Kissimmee is minutes from some of the most popular theme parks in the world. From exploring the four Walt Disney World Resort parks to channeling wizarding magic and superhero power at Universal Orlando Resort and building vacation memories at LEGOLAND Florida, central Florida’s theme parks are not to be missed.

Kennedy Space Center Visitor Complex

Defy gravity and reach for the stars at this gateway to space exploration. The center features behind-the-scenes tours of launch sites and spaceflight facilities, a walk-through rocket garden, astronaut training simulation rides, and the chance to get up close to the Space Shuttle Atlantis.

Florida Everglades

Kissimmee is near Shingle Creek, the headwaters to the Florida Everglades, sometimes called the Sea of Grass. Kayaking in the calm waters beneath a quiet forest of cypress trees is an ideal way to learn more about this unique ecosystem and the many birds, frogs, and alligators who make it their home. Or take a swamp tour on an airboat and leave the driving to someone else.

Destinations to explore

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