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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.

Condo in Kissimmee
An Orlando Adventure with All the Extras. Parking & resort fees included. Star Island, a 5 star resort located Just 10 minutes from Walt Disney World® in popular Kissimmee. It offers so many fun on-site amenities & activities, it actually rivals the magic of Orlando itself. Enjoy the resort at a fraction of the parks. amenities : 2 pools, SPA's, Fitness center, Golf-Driving range, Tennis and Basketball Courts, Pickle Ball courts, Volleyball courts, Water sports, Pool Bar, Ping Pong, Game Room
ﺩ.ﺇ643 per night
Guest suite in Kissimmee
Fully independent guest suite
Relax in this quiet, sleek space. Located in Kissemee, it is a cozy and comfortable space for spend a few unforgettable days of vacation. Our private space has a spacious bedroom and it has a bed in the, bathroom,kitchen and a large patio where you can share with your friends and loved ones. Guests have free access. This is also close to major Disney parks and other Orlando attractions.
ﺩ.ﺇ189 per night
Loft in Orlando
Conveniently located between Downtown’s Lake Eola and the foodie-friendly Milk District, this beautifully unique space features an open floor plan with floor to ceiling windows allowing natural light to fill the space. You’re only a short drive to upscale Winter Park restaurants and the vibrant Thornton Park art scene.
ﺩ.ﺇ470 per night

Stay near Kissimmee's top sights

Medieval Times Dinner & Tournament347 locals recommend
Walmart Supercenter44 locals recommend
Silver Spurs Arena9 locals recommend
FantasyWorld Resort7 locals recommend
Give Kids The World Village7 locals recommend
Osceola Heritage Park12 locals recommend

Other great vacation rentals in Kissimmee

Tiny home in Kissimmee
Small Cottage - clean, cozy and safe
ﺩ.ﺇ256 per night
Loft in Orlando
Contemporary Loft Near Downtown
ﺩ.ﺇ411 per night
Hotel room in Orlando
PentHouse Suite with 2X View
ﺩ.ﺇ804 per night
Apartment in Orlando
Calena Romantic, Contemporary Studio W/Terrace ❤️❤️
ﺩ.ﺇ375 per night
Townhouse in Davenport
No Airbnb Fees! Private Pool in Resort /Clubhouse.
ﺩ.ﺇ640 per night
Condo in Kissimmee
Amazing Resort Condo Near Disney.
ﺩ.ﺇ479 per night
Apartment in Davenport
Modern Resort 1BDApt near Disney
ﺩ.ﺇ410 per night
Condo in Orlando
Last minute discount - Studio close to Universal
ﺩ.ﺇ316 per night
Townhouse in Kissimmee
Modern & Cozy Townhome at Storey Lake
ﺩ.ﺇ767 per night
Condo in Orlando
Wyndham Bonnet Creek ツ 1 Bedroom Deluxe!
ﺩ.ﺇ437 per night
Apartment in Kissimmee
Boho Style Studio Apartment
ﺩ.ﺇ233 per night
Apartment in Kissimmee
King Bed and Close to Disney
ﺩ.ﺇ332 per night

Quick stats about vacation rentals in Kissimmee

Total rentals

7.2K properties

Rentals with dedicated workspaces

3.6K properties have a dedicated workspace

Rentals with a pool

6.4K properties have a pool

Pet-friendly rentals

1K properties allow pets

Family-friendly rentals

6.2K properties are a good fit for families

Total number of reviews

187K reviews

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.

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.

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.

Destinations to explore

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  5. Kissimmee