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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
Laptop-friendly workspace
Pool
Private bathroom

Stay near Kissimmee's top sights

The Hideaway Club House at Storey Lake5 locals recommend
Kissimmee Lakefront Park171 locals recommend
Silver Spurs Arena9 locals recommend
Kissimmee Gateway Airport4 locals recommend
Gatorland417 locals recommend
Loop West Shopping Center256 locals recommend

Private vacation rentals in Kissimmee

Superhost
A private pool is surrounded by a screened enclosure, capturing the evening sky's colors. Natural light filters through the adjacent glass doors, revealing a dining area with patio seating nearby. The tranquil water surface reflects the vibrant hues of sunset.
Home in Kissimmee
4.83 out of 5 average rating, 6 reviews

Cute Vacation Home Very Close to Disney

Superhost
An outdoor space features a spacious pool surrounded by a sunbathing area. A covered seating area offers shade under a large umbrella, while palm trees add a touch of greenery. The screen enclosure provides protection while allowing for natural light and fresh air.
Home in Kissimmee
5 out of 5 average rating, 3 reviews

Dream vacation, near Disney

Superhost
Home in Davenport
4.76 out of 5 average rating, 68 reviews

Casa vacacional

Guest favorite
A private pool area is surrounded by a screened enclosure, featuring a refreshing swimming pool and a spa. Lounge chairs are provided for relaxation, while the patio areas showcase ample sunlight and a serene outdoor environment.
Villa in Davenport
4.9 out of 5 average rating, 10 reviews

Spacious Multi Family Villa- 6Br Sunny Pool Deck!

Guest favorite
Vacation home in Kissimmee
4.83 out of 5 average rating, 104 reviews

Nice & Cozy Home near Disney

Guest favorite
A clear no smoking sign is displayed on the door, emphasizing a strict no smoking policy, including e-cigarettes. Through the window, a glimpse of the private heated pool can be seen, surrounded by trees and landscaped areas.
Home in Kissimmee
4.88 out of 5 average rating, 248 reviews

Private Heated Pool & Hot Tub; 6 miles to Disney

Guest favorite
A private pool area is enclosed with mesh screening, featuring clear blue water. Two lounge chairs are positioned beside the pool on a sunlit patio. A view of a grassy area and trees is visible through the enclosure.
Home in Kissimmee
4.88 out of 5 average rating, 188 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

Superhost
Home in Four Corners
4.88 out of 5 average rating, 48 reviews

H2412T-Windsor at Westside Resort/POOL/Water Park

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Pet-friendly vacation rentals in Kissimmee

Guest favorite
The bright living area features a deep green sofa, a round woven coffee table, and two yellow chairs. A large screen TV is mounted on the wall. Natural light enters through multiple windows, highlighting the neutral decor and welcoming atmosphere.
Townhouse in Orlando
4.98 out of 5 average rating, 85 reviews

May Deals | Downtown Gem | Sleeps 10

Top guest favorite
A spacious pool area features a large swimming pool surrounded by comfortable lounge chairs and a hot tub. The hot tub bubbles gently, and the area is enclosed by a screened patio, providing privacy and protection from insects.
Home in Kissimmee
4.92 out of 5 average rating, 134 reviews

Disney Playhouse, Private Pool & Spa, Near Disney

Top guest favorite
A charming exterior of a two-story home showcases a welcoming entrance with a lit doorway. Lush greenery, including palm trees, frames the path leading up to the door. The warm exterior is highlighted by soft illumination, creating an inviting atmosphere.
Townhouse in Kissimmee
5 out of 5 average rating, 13 reviews

MY HAPPY PLACE 5 Near Celabration and Disney

Guest favorite
A bright living area features a light-colored couch with decorative cushions, a patterned armchair, and a wooden coffee table. Natural light enters through large windows adorned with blinds. A ceiling fan hovers above, and a potted plant adds a touch of greenery.
Apartment in Kissimmee
4.91 out of 5 average rating, 113 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

Guest favorite
The image displays a modern home with a private pool, surrounded by a screened enclosure. Lounge chairs are positioned near the inviting water, reflecting the soft hues of sunset. A well-maintained exterior showcases a spacious driveway and lush grass, inviting guests to relax and enjoy.
Home in Kissimmee
4.87 out of 5 average rating, 167 reviews

Close to Disney!

Superhost
A spacious bedroom is presented with a king-sized bed adorned with decorative pillows. Elegant curtains frame a window, allowing natural light to enhance the warm tones of the room. An accent chair and lamp are positioned beside the bed, contributing to a cozy ambiance.
Villa in Kissimmee
5 out of 5 average rating, 3 reviews

Westgate Resort/Water Park Onsite Included

Superhost
The exterior of a newly remodeled mobile home is shown, featuring a covered porch with steps leading to the entrance. Soft green grass and a palm tree add to the inviting appearance, while nearby trees provide a natural backdrop. The home is set in a mobile home park.
Home in Orlando
4.63 out of 5 average rating, 56 reviews

NEWLY remodeled PET FRIENDLY 2br/1bath by OIA

Superhost
An outdoor seating area features a dining table surrounded by teal chairs, inviting relaxation. String lights illuminate the space, which overlooks a swimming pool and lush greenery. A cozy double hammock is positioned nearby, contributing to a peaceful ambiance during sunset.
Home in Kissimmee
4.72 out of 5 average rating, 96 reviews

Southwest facing pool! 5 Miles from Disney.

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Homes in Kissimmee

Top guest favorite
A private pool area is showcased, featuring a clear blue pool surrounded by a screened enclosure. Comfortable lounge chairs in turquoise are positioned beside the pool. A serene pond and lush greenery are visible beyond the enclosure, providing a calm backdrop.
Home in Kissimmee
4.93 out of 5 average rating, 136 reviews

(Discounted Rates) Vacation Home (4 Miles Disney)

Guest favorite
Home in Kissimmee
4.95 out of 5 average rating, 21 reviews

Beautiful Gated Home near Disney and Universal

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
4.83 out of 5 average rating, 136 reviews

Orlando Home with Private Pool & Game Room !

Guest favorite
A vibrant water play area features a colorful pirate ship surrounded by palm trees and outdoor lounge seating. A slide extends from the ship into a shallow splash zone, inviting family fun. Bright umbrellas provide shade in the background, enhancing the lively atmosphere.
Home in Davenport
5 out of 5 average rating, 18 reviews

New Family friendly townhome.

Guest favorite
A large two-story home is showcased with a well-maintained lawn and framed by palm trees. The exterior features a mix of light and dark colors, with a welcoming front porch and bright exterior lights. A driveway leads to a spacious garage, enhancing the home's curb appeal.
Home in Davenport
4.77 out of 5 average rating, 114 reviews

There is no other place you want to be than here.

Guest favorite
A private pool area is enclosed by a safety screen, offering a view of the inviting water. Surrounding seating arrangements invite relaxation under the sun, with a combination of lounge chairs and dining space visible. Nearby, the exterior of the villa showcases two stories beneath a partially cloudy sky.
Home in Kissimmee
4.96 out of 5 average rating, 25 reviews

Spacious 5BR Villa with Pool, Close to Disney Fun!

Superhost
The exterior of the villa features a light-colored facade with a distinctive archway entrance and blue front door. Lush greenery surrounds the entrance, and palm trees are visible, adding to the welcoming feel. A paved driveway leads up to the home.
Home in Davenport
4.83 out of 5 average rating, 133 reviews

Jaw Dropping 5 Bed 4 Bath Home in Hampton Lakes

Guest favorite
The entrance of a gated community is framed by tall palm trees against a clear blue sky. Decorative stone pillars mark the entryway, with lush greenery and vibrant landscaping visible along the driveway. Cloud formations add texture to the scenic backdrop.
Home in Davenport
4.83 out of 5 average rating, 101 reviews

Family Home Gated 10 Beds Pool Disney 7 miles.

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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 Floridaā€™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 Kissimmeeā€™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 parkā€™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 Kissimmeeā€™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 hourā€™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 Kissimmeeā€™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 Americaā€™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 Floriaā€™s native wildlife habitats. Tall, untamed grass pokes through the parkā€™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 parkā€™s main, elevated viewing platform, where you may be able to spot one of Floridaā€™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 90Ā°F (32Ā°C) and milder winters averaging around 60Ā°F (15Ā°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 3,470 house rentals, over 490 apartment rentals to over 740 villa 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.

Destinations to explore

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  3. Florida
  4. Osceola County
  5. Kissimmee