Vacation rentals in Kissimmee

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Top-rated vacation rentals in Kissimmee

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

Guest favourite

Cottage in Kissimmee

4.98 out of 5 average rating, 134 reviews

Runaway Beach Club Private Patio:Disney, Universal

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

Sep. 11 – 18

$207 CAD per night
Guest favourite

Guest suite in Kissimmee

4.83 out of 5 average rating, 501 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers, we offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We are happy to continue offering our apartment with a 5-star cleanliness rating. We offer our home to travelers only-we do not accept local reservations.

Sep. 18 – 25

$110 CAD per night
Guest favourite

Apartment in Kissimmee

4.92 out of 5 average rating, 200 reviews

Modern APT W/ Patio 15 mins from Theme Parks & MCO

Beautiful space where you can spend a beautiful vacation with your loved ones, the space is created with immense love and for you to feel at home. El acceso será autónomo, con llavín inteligente y una entrada completamente independiente y sin restricción de horario . Ofrecemos un patio exterior diseñado para tiempo de descanso,para compartir un café y también para fumar si fuera de su agrado El parqueo está concebido para dos autos y tenemos cámara de seguridad las24h Todo climatizado

Nov. 16 – 23

$191 CAD per night

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

Cottage in Kissimmee

4.94 out of 5 average rating, 364 reviews

Entire Cottage close to Disney, Universal, Airport

Jun. 11 – 18

$164 CAD per night
Guest favourite

Condo in Kissimmee

4.91 out of 5 average rating, 111 reviews

First floor/your Disney escape

Sep. 18 – 25

$179 CAD per night
Guest favourite

Tiny homes in Kissimmee

4.94 out of 5 average rating, 326 reviews

Blue Bungalow Tiny House near all Attractions!!

Mar. 10 – 17

$179 CAD per night
Guest favourite

Tiny homes in Kissimmee

4.9 out of 5 average rating, 433 reviews

ZMZ Tiny House Living! Try it out while at Disney

Feb. 8 – 15

$146 CAD per night
Guest favourite

Tiny homes in Kissimmee

4.95 out of 5 average rating, 142 reviews

Disney Tiny House Getaway!

Oct. 29 – Nov. 5

$150 CAD per night
Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 204 reviews

3 bedroom Villa in Kissimmee

Mar. 19 – 26

$203 CAD per night
Guest favourite

Guesthouse in Four Corners

4.98 out of 5 average rating, 420 reviews

Quiet Room Close to Disney and Attractions

Jul. 31 – Aug. 7

$150 CAD per night
Superhost

Cabin in Kissimmee

4.83 out of 5 average rating, 29 reviews

Romantic Cabin w/ Balcony + Tub + Hammock + Grill

May 11 – 18

$190 CAD per night
Guest favourite

Guesthouse in Orlando

5.0 out of 5 average rating, 44 reviews

Guesthouse hosted by Yadier

Jun. 17 – 24

$180 CAD per night
Superhost

Guest suite in Orlando

4.82 out of 5 average rating, 28 reviews

Beautiful Suite, with independent entrance parking

Dec. 18 – 25

$105 CAD per night
Guest favourite

Condo in Kissimmee

5.0 out of 5 average rating, 7 reviews

Resort Oasis Near Disney World

Sep. 29 – Oct. 6

$195 CAD per night
Guest favourite

Townhouse in Kissimmee

5.0 out of 5 average rating, 9 reviews

Summer Studio at Kissimmee

Jun. 14 – 21

$144 CAD per night

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

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  3. Florida
  4. Osceola County
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