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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.

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.
$51 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.
$130 per night
Condo in Kissimmee
Amazing ❤️ Water View Condo near Disney & Universal
Runaway Beach Club! Orlando, FL Vacation! Beautiful condo with a breath taking view of the lake and 10 minutes from Disney World, close to Universal Studios and 2 minutes from Walmart grocery store.
$127 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

Hotel room in Orlando
PentHouse Suite with 2X View
$219 per night
Loft in Orlando
Contemporary Loft Near Downtown
$116 per night
Condo in Kissimmee
Lux golf view and amazing pools
$110 per night
Condo in Orlando
Discounted - Deluxe Studio:Lakeview, parking, pool
$80 per night
Condo in Kissimmee
$175 per night
Tiny home in Kissimmee
Cozy Cottage by Disney. Clean, Safe, Convenient
$69 per night
Home in Kissimmee
1676ST-Best Home in Storey Lake Resort Near Disney
$297 per night
Townhouse in Davenport
No Airbnb Fees! Private Pool in Resort /Clubhouse!
$181 per night
Condo in Kissimmee
Amazing Resort Condo Near Disney.
$139 per night
Townhouse in Kissimmee
Modern & Cozy Townhome at Storey Lake
$209 per night
Apartment in Davenport
Modern Resort 1BDApt near Disney
$112 per night
Condo in Orlando
Wyndham Bonnet Creek ツ 1 Bedroom Deluxe!
$119 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.

Frequently Asked Questions

  • How is the weather in Kissimmee?

    Kissimmee boasts a tropical climate, with hot, humid summers reaching 90°F (32°C) and milder winters averaging around 60°F (15°C). Rainfall is more frequent in the summer, while winter tends to be drier.

  • What are some of the best things to do in Kissimmee?

    Popular activities in Kissimmee include exploring the Old Town, a recreated Florida town full of shops and restaurants, taking a thrilling airboat tour on Lake Tohopekaliga, or enjoying a round of golf at one of the city's many golf courses.

  • What is the best time of year to visit Kissimmee?

    The most popular time to visit Kissimmee is in the summer, particularly between March and August. During this period, the city hosts local events such as the Kissimmee Sunshine Regional Chili Cook-Off and the Silver Spurs Rodeo.

  • What are the best places to stay in Kissimmee?

    Celebrate, a family-friendly community, is often recommended for its proximity to theme parks. Downtown Kissimmee is popular for its vibrant nightlife and historic landmarks. West Kissimmee, located close to a number of natural attractions, is also frequently suggested.

  • What are the best places to visit in Kissimmee?

    Popular places to visit in Kissimmee include the Kissimmee Lakefront Park, the Osceola County Historical Society Pioneer Village, and Gatorland, a wildlife preserve and theme park.

  • What are some hiking trails in Kissimmee?

    Kissimmee has a variety of hiking trails such as the Shingle Creek Regional Trail for scenic views of natural Florida or the Disney Wilderness Preserve which is home to numerous species of plants and animals.

  • What are some family activities to do in Kissimmee?

    Families in Kissimmee can explore numerous attractions including the interactive exhibits at the Museum of Military History, a fun-filled day at Fun Spot America amusement park, or a chance to spot native Florida wildlife at the Wildlife Refuge.

  • What are some of the best day trip ideas in Kissimmee?

    Popular day trips from Kissimmee often include a visit to Orlando, just 17 miles (27 km) away, to experience its world-renowned theme parks. Alternatively, the beautiful beaches of Clearwater are just 90 miles (145 km) away.

  • How much does it cost to stay in vacation home rentals in Kissimmee?

    Experience the best of Kissimmee with our vacation home rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation home rentals with a dedicated workspace in Kissimmee?

    Yes! Work meets play with ease at over 20 vacation home rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee