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Vacation rentals in Kissimmee

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Kissimmee vacation rentals

Self check-in
Pet friendly
Pool
Laptop-friendly workspace
Private bathroom

Stay near Kissimmee's top sights

Kissimmee Lakefront Park138 locals recommend
Kissimmee Gateway Airport8 locals recommend
Gatorland418 locals recommend

House rentals in Kissimmee

Guest favorite
A tranquil swimming pool is illuminated in blue light, surrounded by a smooth deck. Inflatable pool toys float on the water, while a sun umbrella and lounge chairs provide a place to relax. The area is enhanced by palm trees and soft night lighting.
Home in Kissimmee
4.84 out of 5 average rating, 140 reviews

Beautiful Vacation Home With Private Pool.

Guest favorite
A spacious bedroom is furnished with a large bed, adorned with soft linens and a light throw. Natural light enters through a window, which is framed by neutral-toned walls. Two closet doors are visible, and wooden furniture adds warmth to the space.
Home in Davenport
4.9 out of 5 average rating, 29 reviews

Lovely 3BD House w/ private pool

Guest favorite
A vibrant children's themed bedroom showcases a two-story castle adorned with princess graphics. A pink slide is positioned beside the castle, inviting playful adventures. The room is brightly lit and features colorful wall murals.
Home in Davenport
4.94 out of 5 average rating, 31 reviews

Disney Dream Escape

Guest favorite
A vibrant game room showcases colorful decor and themed elements featuring popular gaming icons. An inviting heated pool and hot tub are visible outside, surrounded by lush greenery and a spacious deck. The image conveys a lively atmosphere ideal for family entertainment.
Home in Kissimmee
4.97 out of 5 average rating, 77 reviews

Pool | Themes | Game Room

Guest favorite
An aerial view showcases Mickey's Lakeside Villa, characterized by a modern roof and a driveway leading to the entrance. Lush green landscaping surrounds the home, with a tranquil lake in the background featuring a decorative fountain amidst the scenic view.
Home in Kissimmee
4.96 out of 5 average rating, 54 reviews

Mickey’s Lakeside Villa w/ pool near Disney!

Superhost
An inviting pool area is enclosed by a sturdy screen, featuring a clear blue pool and a cascading spa. Palm trees and neatly trimmed shrubs surround the space, with twinkling lights strung overhead. A serene sunset sky adds a colorful backdrop to the relaxing atmosphere.
Home in Kissimmee
4.6 out of 5 average rating, 5 reviews

Family Fun Retreat w/ Game Room & Themed Bedrooms!

Superhost
A vibrant game room features colorful murals inspired by a classic video game theme. A foosball table and a pool table are provided for entertainment, while a wall-mounted TV displays gaming visuals. The room is illuminated with soft lighting, creating a fun and inviting atmosphere.
Home in Kissimmee
4.91 out of 5 average rating, 23 reviews

Beautiful Family Retreat in Windsor at Westside

Top guest favorite
A screened lanai features a large swimming pool, surrounded by a paved deck and four patio loungers. The tranquil water view is visible through the mesh enclosure, with colorful skies reflecting at sunset.
Home in Kissimmee
5 out of 5 average rating, 18 reviews

Ohana Lakeside Retreat

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Family friendly vacation rentals in Kissimmee

Guest favorite
The exterior of the home is shown, featuring a tiled roof and lush landscaping. Tropical plants and vibrant flowers surround the property, while Spanish moss hangs from a nearby tree. Clear blue skies create a bright atmosphere, highlighting the welcoming entrance.
Home in Kissimmee
4.89 out of 5 average rating, 172 reviews

VerandaPalms/HeatedPool/Carpet free/NearDisney

Top guest favorite
A private pool area is enclosed by a screened lanai, featuring a sparkling pool and a relaxing spa. A circular glass-top table with four cushioned chairs is positioned beside the pool, providing a comfortable spot for outdoor dining and relaxation.
Home in Kissimmee
4.92 out of 5 average rating, 146 reviews

Private Pool & Spa, Close Disney, Disney Playhouse

Superhost
The resort clubhouse is showcased at sunset, featuring a large pool with lounge chairs arranged around it. Vibrant colors fill the sky, reflecting on the water's surface. Palm trees frame the scene, enhancing the tropical ambiance of the area.
Townhouse in Kissimmee
4.89 out of 5 average rating, 136 reviews

"Sunset Hideaway" - Enchanted Lakeside Retreat

Top guest favorite
A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.
Villa in Kissimmee
4.86 out of 5 average rating, 413 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

Superhost
A private screened pool area features a blue pool surrounded by several lounge chairs and a dining set. Lush greenery is visible beyond the enclosure, providing a natural backdrop. The sun shines brightly through the mesh, creating a bright and open space for relaxation.
Home in Kissimmee
4.89 out of 5 average rating, 183 reviews

Luxurious Private Retreat w/Spa & Saltwater Pool

Top guest favorite
A private pool is visible, surrounded by a screened-in patio. Lush green grass and trees form a natural backdrop, providing a serene view. Sunlight filters through the foliage, creating a peaceful atmosphere for relaxation.
Home in Davenport
4.93 out of 5 average rating, 206 reviews

Orlando 5BD+Pool, Near Disney & ChampionsGate Golf

Superhost
A private pool is set within a screened enclosure, overlooking tranquil waters. Lounge chairs with striped cushions are arranged near the pool, and lush greenery frames the serene view, creating a relaxing outdoor space.
Villa in Kissimmee
4.88 out of 5 average rating, 110 reviews

Beautiful Home with Pool near Golf & Disney

Guest favorite
A private screened-in pool area is showcased, featuring a turquoise swimming pool and a furnished patio. Four chairs surround a glass-top table, beneath a blue umbrella. A privacy fence surrounds the yard, providing a tranquil atmosphere.
Home in Kissimmee
4.8 out of 5 average rating, 290 reviews

3 bedroom Orlando Florida pool home

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Pet-friendly vacation rentals in Kissimmee

Guest favorite
A private pool area is enclosed with a screened structure, featuring a pool with a colorful float. Loungers are placed along the pool's edge, with views of the serene lake and greenery just beyond. The space invites relaxation and enjoyment.
Villa in Kissimmee
4.87 out of 5 average rating, 133 reviews

Villa, Games, Theater, Nr Disney, Great Pool Heat

Top guest favorite
The exterior of a single-story home is presented, featuring a paved driveway leading to a two-car garage. Lush green grass surrounds the house, and palm trees are positioned near the entrance. A colorful sunset sky provides a picturesque backdrop.
Villa in Kissimmee
4.99 out of 5 average rating, 117 reviews

Beautiful home. Private pool. Close to Disney!

Superhost
A screened lanai features a refreshing swimming pool, offering views of a quietly flowing pond surrounded by lush greenery. The space is illuminated by natural light filtering through the mesh enclosure, inviting relaxation amid nature.
Home in Kissimmee
4.81 out of 5 average rating, 106 reviews

Nice pond view home with pool and outdoor theatre!

Guest favorite
A spacious living area features a sleek, curved sectional sofa in light grey, centered around a round white coffee table atop a textured area rug. Accents include vibrant orange armchairs and modern light fixtures, with a large painting adding a touch of color to the wall.
Home in Four Corners
4.9 out of 5 average rating, 192 reviews

Luxury 6 Bdr Family Getaway~Private Pool

Superhost
An engaging Star Wars-themed game room features a foosball table, arcade machines, and a spacious seating area. Murals depict scenes from the franchise, with screens displaying games. The room is designed for fun and entertainment, offering a vibrant environment for guests.
Home in Kissimmee
4.82 out of 5 average rating, 141 reviews

Orlando Home with Private Pool & Game Room !

Superhost
A cozy living area is highlighted by a decorative wall, a TV mounted above a light-colored cabinet, and a plush seating arrangement. A fire pit with glowing embers is visible, providing a warm ambiance. A game table with two chairs and a pool table is present, alongside a screened pool area showcasing a sunset view.
Home in Kissimmee
4.87 out of 5 average rating, 190 reviews

Waterfront retreat,KING Bed,Heated Pool & Fire Pit

Guest favorite
A private movie theater features a 150-inch screen displaying a Disney image. Black walls and hardwood flooring create a modern atmosphere. Comfortable reclining seats with cup holders are arranged for a cinematic experience, ensuring a cozy and immersive viewing environment.
Villa in Kissimmee
4.82 out of 5 average rating, 249 reviews

150 Inch 4K Movie Theater Pool & Spa sleeps 16

Top guest favorite
An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.
Villa in Kissimmee
4.97 out of 5 average rating, 122 reviews

*Brand New!* Minutes to Disney + Free Resort!

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Quick stats about vacation rentals in Kissimmee

  • Total rentals

    7.2K properties

  • Total number of reviews

    242K reviews

  • Family-friendly rentals

    6.1K properties are a good fit for families

  • Pet-friendly rentals

    1.1K properties allow pets

  • Rentals with a pool

    6.5K properties have a pool

  • Rentals with dedicated workspaces

    3.9K properties have a dedicated workspace

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.

  • What types of vacation rentals are available in Kissimmee?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Kissimmee. From over 740 villa rentals, over 490 apartment rentals to over 3,470 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

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

    Yes! Work meets play with ease at over 3,930 vacation rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.

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