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Vacation rentals in Kissimmee

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Top-rated vacation rentals in Kissimmee

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

Condo · Kissimmee
* Condo near Disney Parks with Free Shuttle *
Relaxing resort only 8 min away from Disney World, 13 from Seaworld and 19 from Universal Studios. The 1 bedroom apartament includes a kitchen, a living room with a TV and a sofa that turns into bed, dining room, closets, 1 ensuite bedroom with a queen bed and TV, bathtub and a balcony. There are many outdoors pools and jacuzzis, a playground and outdoors grills as well as gym.
Oct 22 – 29
$65 per night
Superhost
Private room · Kissimmee
Enjoy Orlando with us/Enjoy Orlando as a family
Very comfortable queen size couples room, 30 minutes from Los Parques. If you need to accommodate someone else, we can offer you an inflatable mattress, with an extra charge. Place for couple, queen size very comfortable, at only 30 minutes from theme parks.. . If to You need accommodates one more person we can provide a air mattress, with addicional fee.
Jan 30 – Feb 6
$35 per night
Superhost
Private room · Kissimmee
Private Room in Orlando/Kissimmee (2Twins) T1
Vacation home for people touring the Orlando and Kissimmee area. This beautiful home with excellent amenities is located at Bella Vida Resort only 5 minutes away from Walmart and Wawa and 15-20 minutes from Disney! It is very close to restaurants, theme parks and the US-192. You may consider this your home away from home. Our guests are our number one priority. We treat all with the best attitude, always making sure they feel welcome.
Jul 30 – Aug 6
$36 per night
Superhost

Vacation rentals for every style

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Stay near Kissimmee's top sights

Photo of Kissimmee Lakefront Park
Kissimmee Lakefront Park40 locals recommend
Photo of Skate Reflections
Skate Reflections4 locals recommend
Photo of Medieval Times Dinner & Tournament
Medieval Times Dinner & Tournament105 locals recommend
Photo of Give Kids The World Village
Give Kids The World Village3 locals recommend
Photo of Walmart Supercenter
Walmart Supercenter11 locals recommend
Photo of Osceola Heritage Park
Osceola Heritage Park5 locals recommend

Houses in Kissimmee

Private room · Kissimmee
comfortable private bedroom near Disney
Oct 9 – 16
$42 per night
Superhost
Private room · St. Cloud
Just a room. 30 miles to Disney. 40 miles to ocean
Dec 16 – 23
$33 per night
Superhost
Home · Kissimmee
Casita Disney! Cozy Boho Townhouse near Disney
Aug 10 – 17
$118 per night
Superhost
Private room · St. Cloud
Immaculate Private Bedroom 2 - Twin Bed
Nov 3 – 10
$32 per night
Superhost
Home · Kissimmee
Comfortable 3-bedrooms Pet friendly Disney 8 mi
Nov 30 – Dec 7
$95 per night
Superhost
Private room · Kissimmee
Single Private Bedroom with a Queen Bed (Room 2)
Nov 24 – Dec 1
$30 per night
Private room · Kissimmee
Double Cozy Bedroom + Clubhouse Resort
Dec 13 – 20
$37 per night
Superhost
Private room · Kissimmee
Bedroom, private bath, vacation home near Disney 3
Nov 29 – Dec 6
$50 per night
Superhost
Private room · Kissimmee
Bedroom, private bath in mansion style near Disney
Feb 21 – 28
$66 per night
Superhost
Home · Kissimmee
3 bedroom Villa in Kissimmee
Sep 8 – 15
$85 per night
Superhost
Home · Kissimmee
Beautiful Pool Home 9 beds sleeps 14 near Disney.
Sep 23 – 30
$137 per night
Superhost
Private room · Kissimmee
Private bedroom in beautiful house 1
Sep 2 – 9
$35 per night
Superhost

Villa rentals in Kissimmee

Villa · Kissimmee
Newly furnished,4 Bed villa ft Harry Potter room
Sep 10 – 17
$190 per night
Villa · Kissimmee
Disney Dream Villa- 10 Minutes From Disney!
Sep 6 – 13
$228 per night
Superhost
Villa · Kissimmee
Sleeps 20✦Free Pool Heat✦15 min to Disney✦Hot Tub
Oct 26 – Nov 2
$271 per night
Superhost
Private room · Kissimmee
#2 private bath one king size bed 9 mins 2 Disney
Oct 7 – 14
$47 per night
Superhost
Villa · Kissimmee
7BDR with Movie Theater, Pool/Spa, close to DISNEY
Sep 2 – 9
$292 per night
Superhost
Villa · Davenport
Brand New 10BD Mansion at Windsor Island Resort
Sep 8 – 15
$320 per night
Superhost
Villa · Kissimmee
Relaxing Villa in Kissimmee #02227
Jul 15 – 22
$59 per night
Villa · Kissimmee
Star Wars 🔥 Game room 🕹Pool 💦Movie Room 🍿Close to Parks!!
May 26 – Jun 2
$454 per night
Superhost
Villa · Kissimmee
★Completely Renovated★ 3 mi to Disney+Free Resort!
May 12 – 19
$317 per night
Superhost
Villa · Kissimmee
Lake View Luxury/near disney/2876 free water park
Nov 29 – Dec 6
$476 per night
Superhost
Villa · Kissimmee
Villa near Disney 4Bd Luxury Villa Private pool
Jul 9 – 16
$146 per night
Villa · Kissimmee
Beautiful home. Private pool. Close to Disney!
Aug 29 – Sep 5
$190 per night
Superhost

Weekly rentals in Kissimmee

Shared room · Kissimmee
20 minutes away from Disney
Apr 2 – 9
$28 per night
Private room · Kissimmee
Double Cozy Room 2 + Clubhouse Resort
Oct 25 – Nov 1
$32 per night
Superhost
Private room · Kissimmee
King White Suite + Clubhouse Resort
Oct 20 – 27
$49 per night
Superhost
Private room · Kissimmee
Single Private Bedroom with a Queen Bed (Room 3)
Nov 23 – 30
$29 per night
Private room · Kissimmee
Amazing and Central Private Room-Kissimmee
Dec 7 – 14
$35 per night
Superhost
Private room · Kissimmee
#Room - Comfortable Mickey’s King bed
Nov 5 – 12
$41 per night
Superhost
Home · Kissimmee
Lovely Luxury 3-Bedroom 2 Bath Full House
Apr 14 – 21
$81 per night
Superhost
Private room · Kissimmee
Master Suite
Nov 1 – 8
$47 per night
Private room · Four Corners
Beach Room near Disney +Resort
May 22 – 29
$43 per night
Private room · Kissimmee
Room minutes away from Kissimmee lakefront park
Mar 17 – 24
$40 per night
Superhost
Private room · Kissimmee
RING A DING DING RED’s MY THING
Dec 1 – 8
$35 per night
Private room · Orlando
Decorated room for 2 - the desert in a pool house!
Jan 25 – Feb 1
$45 per night
Superhost

Your guide to Kissimmee

All About Kissimmee

Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.

Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.


When is the best time to stay in a vacation rental in Kissimmee?

Kissimmee weather stays fairly warm throughout the year, but visitors should plan for a few rainy days here and there. Summers are usually hot and humid, and on a sunny day, a visit to Cocoa Beach is about an hour’s drive away from most Kissimmee vacation rentals. Spring weather is cooler but warm enough to kayak through the headwaters of the Florida Everglades at the Shingle Creek Regional Park. On a typical winter or fall day, the weather is cool and comfortable enough to be outdoors. During these two seasons, you can plan a picnic at the serene Brownie Wise Park facing Kissimmee’s massive Lake Tohopekaliga.


What are the top things to do in Kissimmee?

Kissimmee Lakefront Park

The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.

Museum of Military History

Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.

Twin Oaks Conservation Area

The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.

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