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
Close To Disney! 3 Bedroom Condo in Windsor Palms
Whatever your vacation style, our family-friendly 3 bedroom 2 bath top floor spacious condo, located in picturesque Windsor Palms gated community, will be waiting to welcome you home! Visit Disney World Attractions just 4.9 miles away, or grab a drink from the Tiki bar & relax by the pool. Whatever your style, this split bedroom privacy floor plan is perfect for traveling with family or friends. Equipped kitchen, free high-speed wifi, TVs in bedrooms, & more! *CLICK SHOW MORE FOR FULL DETAILS!*
Aug. 25 – Sep. 1
$181 CAD per night
4.96 out of 5 average rating, 138 reviews
Superhost
Condo in Kissimmee
Beautiful Resort-Style Condo with Waterpark!
JJC Vacation Home is a gated resort-style condo that has everything you need to have the best vacation! The condo is near all main attractions, fully equipped kitchen, a lazy river, water slides, pool, splash area, mini golf, fitness center, kayak/canoe rental, bar, food, and more! Our Star Wars theme room with *glow in the dark* stars wall will make you feel like you're floating in space! Complimentary coffee/tea station. Relax while having a cup as you look at the view from the balcony.
Oct. 15 – 22
$231 CAD per night
4.85 out of 5 average rating, 153 reviews
Guest favourite
Condo in Kissimmee
First floor/your Disney escape
Our condo is located on the first Floor at resort-style community (with No Resort FEES and FREE parking) with a nice clubhouse featuring a game room, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort also features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, carwash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.
Sep. 14 – 21
$171 CAD per night
4.92 out of 5 average rating, 110 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
Cabin in Davenport
$89! Cozy Cabin- Disney 20 Miles Away!
May 25 – Jun. 1
$171 CAD per night
4.92 out of 5 average rating, 163 reviews
Guest favourite
Guest suite in Kissimmee
Newly renovated near Disney and Universal Orlando
Apr. 22 – 29
$122 CAD per night
4.94 out of 5 average rating, 117 reviews
Superhost
Home in Kissimmee
3 bedroom Orlando Florida pool home
Nov. 5 – 12
$195 CAD per night
4.78 out of 5 average rating, 253 reviews
Guest favourite
Cottage in Davenport
$79! Cozy Cottage + Outdoor Fun -Close to Disney!
May 10 – 17
$154 CAD per night
4.92 out of 5 average rating, 122 reviews
Superhost
Condo in Kissimmee
2BD/2BA Storey Lake condo close to Disney #51
Sep. 2 – 9
$240 CAD per night
4.79 out of 5 average rating, 204 reviews
Guest favourite
Tiny homes in Kissimmee
Disney Tiny House Getaway!
Nov. 10 – 17
$151 CAD per night
4.95 out of 5 average rating, 141 reviews
Guest favourite
Apartment in Kissimmee
20min to Disney/Free Parking/Gym/Pool/Gated
May 27 – Jun. 3
$173 CAD per night
4.95 out of 5 average rating, 20 reviews
Guest favourite
Tiny homes in Kissimmee
Luxury Tiny Cottage. Only 5 miles from Disney!
Aug. 28 – Sep. 4
$164 CAD per night
4.98 out of 5 average rating, 40 reviews
Guest favourite
Guesthouse in Orlando
Guesthouse hosted by Yadier
May 19 – 26
$195 CAD per night
5.0 out of 5 average rating, 44 reviews
Guest favourite
Townhouse in Kissimmee
Summer Studio at Kissimmee
Aug. 1 – 8
$135 CAD per night
5.0 out of 5 average rating, 9 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
Superhost
Apartment in Kissimmee
2 Bedroom-2 Bathroom Spacious Condo Near Disney
Jan. 2 – 9
$178 CAD per night
5.0 out of 5 average rating, 3 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