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.

Private room · Kissimmee
Single Private Bedroom with a Queen Bed (Room 3)
Relax with the whole family at this peaceful place to stay.
ﺩ.ﺇ111 per night
Private room · Kissimmee
Cozy Suite at Compass Bay Resort
Relax in this beautiful and charming suite nicely decorated with a full bathroom inside. We are located near all major restaurants and shops.
ﺩ.ﺇ157 per night
Entire townhouse · Kissimmee
Bella home w/private pool close to theme parks
Stylish lake townhome with a private pool located in Bella Vida Resort. Bella Vida Resort is a Mediterranean style community. Our lovely townhome is located is conveniently located next to US192, and near to the Happiest Place on Earth Disney Theme Parks (~ 16 minutes) and Orlando’s world-famous outlets (~ 27 minutes)
ﺩ.ﺇ511 per night

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

Shared room · Kissimmee
20 minutes away from Disney
ﺩ.ﺇ103 per night
Entire home · Kissimmee
Wizarding Home 10m-Harry Potter Universal Orlando™
ﺩ.ﺇ448 per night
Entire home · Kissimmee
ﺩ.ﺇ589 per night
Entire home · Kissimmee
5Bedrooms/5 Bathrooms Storey Lake (4777 KC)
ﺩ.ﺇ495 per night
Entire home · Davenport
6Bedrooms/ 4.5 Bathroom Windor Island (1221 AB)
ﺩ.ﺇ526 per night
Entire home · Four Corners
ﺩ.ﺇ495 per night
Entire home · Kissimmee
ﺩ.ﺇ495 per night
Entire home · Kissimmee
SANITIZED Storey Lake, Free Warterpark NC207
ﺩ.ﺇ441 per night
Private room · Intercession City
Room#2 close to Disney, Universal, NO CLEANING FEE
ﺩ.ﺇ130 per night
Entire home · Kissimmee
4Bedrooms/3.5 Bathrooms Solara Resort (9032 EM)
ﺩ.ﺇ379 per night
Entire home · Kissimmee
Cheerful Home W/ Heated Pool | Free Coffee | Ideal for Long Stays!
ﺩ.ﺇ334 per night
Private room · Kissimmee
Rustic White en Suite near Disney with a Pool
ﺩ.ﺇ195 per night

Villa rentals in Kissimmee

Entire villa · Kissimmee
Wizarding Enchanted Castle Lake View 6 BDRM Resort Villa 9mi to Disney 15mi to Wizarding World of Harry Potter
ﺩ.ﺇ492 per night
Entire villa · Kissimmee
Newly furnished,4 Bed villa ft Harry Potter room
ﺩ.ﺇ661 per night
Entire villa · Kissimmee
ﺩ.ﺇ689 per night
Entire villa · Four Corners
Brilliant 7B/5B with Heated Pool, SPA & BBQ Grill
ﺩ.ﺇ745 per night
Entire villa · Kissimmee
Comfortable House Access to the New Story Lake
ﺩ.ﺇ482 per night
Private room · Kissimmee
Private Luxury Suite/Entrance/Bath 5m to Disney1
ﺩ.ﺇ217 per night
Entire villa · Kissimmee
Sleeps 20✦Free Pool Heat✦15 min to Disney✦Hot Tub
ﺩ.ﺇ867 per night
Entire villa · Davenport
ﺩ.ﺇ574 per night
Entire villa · Kissimmee
4547 Modern Disney Sleep24 @StoreyLake Pool*Movie
ﺩ.ﺇ895 per night
Entire villa · Kissimmee
Walt Disney / Universal Orlando Villa: Pool & Spa!
ﺩ.ﺇ376 per night
Entire villa · Kissimmee
4291 - FREE Grill + Resort Included + home🏡 Private Pool/8.5 Miles to DISNEY
ﺩ.ﺇ506 per night
Entire villa · Kissimmee
Amazing House close to Disney. Enjoy Private Pool!
ﺩ.ﺇ599 per night

Weekly rentals in Kissimmee

Entire home · Kissimmee
ﺩ.ﺇ589 per night
Entire home · Kissimmee
New Private Pool Mid Century Home Near Disney Park
ﺩ.ﺇ513 per night
Entire home · Kissimmee
Warm and inviting 4 bedroom home with a large Pool
ﺩ.ﺇ568 per night
Entire home · Kissimmee
Nice pond view home with a pool & outdoor theatre!
ﺩ.ﺇ474 per night
Entire home · Kissimmee
6BR Family Resort Mansion Private Pool/BBQ/More!
ﺩ.ﺇ675 per night
Entire home · Kissimmee
Disney Home! Private Pool/Spa/ New Arcade! 4BR 3BA
ﺩ.ﺇ621 per night
Entire home · Kissimmee
No Airbnb fees! Private Pool/SPA/Game Room on a Resort.
ﺩ.ﺇ810 per night
Private room · Kissimmee
Private room in beautiful house # 2
ﺩ.ﺇ129 per night
Entire home · Polk County
ﺩ.ﺇ495 per night
Entire home · Kissimmee
Magical 5 bedrooms home, with Pool/BBQ near Disney
ﺩ.ﺇ589 per night
Private room · Kissimmee
Rustic Suite with Spa and Pool Near Disney
ﺩ.ﺇ151 per night
Entire home · Kissimmee
ﺩ.ﺇ390 per night

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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