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Vacation rentals in Kissimmee

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Kissimmee vacation rentals

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
The single-story home features a welcoming façade with a brick accent. Lush palm trees frame the entrance, which is highlighted by large windows allowing natural light to filter inside. A manicured lawn and a decorative white planter add charm to the front yard.
Home in Kissimmee
4.95 out of 5 average rating, 216 reviews

Disney Orlando vacation home with private pool 2

ErmelindaRating, 5 stars2 weeks ago
This place was incredible. it turned out more than we expected. we had our 9 year old nephew with us who was celebrating his birthday and that game room was out of this world. Vi and her husband cane out to show us how to operate the video games and my nephew loved the Batman video and that was his favorite and played it all the time and as long as he was aloud to play. I highly recommend this place. We are definitely coming back and hopefully fir a much longer stay.
Guest favorite
A screened-in patio features a private swimming pool and hot tub, surrounded by a tranquil lake view. String lights create a soft illumination against a colorful sunset sky, enhancing the peaceful outdoor setting.
Home in Kissimmee
4.92 out of 5 average rating, 116 reviews

10 min Disney | Lakeview Hot Tub, BBQ | Game Room

CarterRating, 5 stars3 days ago
This was definitely a great place to stay, easy to check in and the host was so responsive! I hosted a birthday party and everyone had an amazing time and had everything they needed.
Guest favorite
An outdoor terrace is showcased with comfortable seating arrangements, featuring woven furniture adorned with soft cushions. A glass coffee table sits at the center, providing a perfect spot for refreshments. The serene view of lush greenery stretches in the background, creating a peaceful setting.
Home in Davenport
4.85 out of 5 average rating, 62 reviews

Escape to Sun~Kissed Paradise

Colin,PRating, 5 stars2 months ago
My family had a wonderful time at this Airbnb! A few favorite things about the place was the balcony, the privacy with no neighbors behind us, and how quiet the neighborhood was. The only complaints from the kids was that there was no park or community pool access. The location is great and not too far from most major attractions. House was clean and very much represented the photos in the listing. Carlos and his team responded very quickly to any requests we had. We would be happy to stay here again!
Guest favorite
A private pool area featuring a clear blue pool with spa and surrounding palm trees. A giant outdoor chess set is visible nearby, along with a colorful tube slide leading to a vibrant bunk bed room. A game table with billiards is also showcased in the movie theater room.
Home in Four Corners
4.96 out of 5 average rating, 178 reviews

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

KaylaRating, 5 stars3 weeks ago
We had such a great time staying at Michael’s place! Our five teenagers were never bored with all of the fun amenities! The kids had a great time with the karaoke machine, arcade games and outdoor area! My husband and I love coffee, so we really appreciated the coffee bar and supplies that were provided. The house was beautiful and Michael was extremely responsive. We would stay again!
Guest favorite
A vibrant game room features colorful murals of popular video game characters, with a bright blue floor and ceiling. A foosball table is positioned near a large television, complemented by bar stools in yellow. A slide adds a playful touch to the fun atmosphere.
Home in Kissimmee
5 out of 5 average rating, 5 reviews

8993-WW 5 Bedroom ALL Suites Pool Home

NinaRating, 5 stars3 weeks ago
Amazing house ! You won’t regret it, kids were in angry to leave Magic Kingdom just to come back to the House lol. Very memorable!
Top guest favorite
A single-story villa features a tiled roof and a charming facade, accompanied by decorative shutters on the windows. A paved driveway leads to a garage, while landscaped greenery offers an inviting appeal. Palm trees stand alongside the home, enhancing the sunny atmosphere.
Home in Davenport
5 out of 5 average rating, 18 reviews

Dream Villa W/ Pool Near Disney

KobeRating, 5 stars5 days ago
Luis was a amazing host his response time was very quick. I would recommend his davenport place to anyone, It was our first time here and he made our dreams come true with the airbnb. It was exactly like the pictures and provided lots of things for us including towels, utensils, etc.
Guest favorite
The exterior of the house showcases a modern design with a paved driveway. A screened pool area features a sunny pool with a floating device and beach ball. Inside, a vibrant game room with a pool table, alongside themed children's bedrooms and a neutral-toned master bedroom, is displayed.
Home in Kissimmee
4.87 out of 5 average rating, 118 reviews

Pool Home! 10 Min from Disney

JadeanneRating, 5 stars3 weeks ago
So happy with our stay, met our needs completely. Beautiful space, great amenities. We really hope to return, Thank you so much
Superhost
The spacious open-plan living area features a large sectional sofa, a sleek coffee table, and a wall-mounted smart TV. A dining area with stylish chairs is visible in the background, along with a modern kitchen including a dining island, illuminated by pendant lights.
Home in Davenport
4.85 out of 5 average rating, 26 reviews

Stunning and modern 4 bedroom home with pool

LizRating, 5 stars4 weeks ago
This place was incredible, as soon as we walked in we were so impressed with the way it was presented. We had arranged for a celebration set up and this was absolutely stunning and all of it blew us all away. The pool and hot spa is definitely a good way to end a busy day. In a good residential area and 40 minutes to Universal Studios. We will definitely re-book when back in Orlando.

Vacation rentals with pools in Kissimmee

Guest favorite
An open living area features a large sectional sofa, perfect for relaxation. A dining table for six is visible, with a modern kitchen in the background. Natural light floods the space, highlighting neutral walls and tiled flooring, creating a welcoming environment.
Home in Kissimmee
4.93 out of 5 average rating, 29 reviews

Cozy 4 bedroom home with pool -Close to everything

EbonyRating, 5 stars3 weeks ago
Host was responsive! Nicely decorated! Clean!
Guest favorite
An outdoor area features a private swimming pool surrounded by tropical landscaping, with a pink float resting in the water. An interior game room displays a space-themed mural and includes various gaming consoles, gaming chairs, and vibrant LED lighting. A cozy lounge area is visible, accented by plush seating.
Home in Kissimmee
5 out of 5 average rating, 6 reviews

Game On! Pool, Game Room & Themes | Near Disney

AlexandraRating, 5 stars5 days ago
The house is beautiful and very clean. There was plenty of room for our family of 11. The game room was fun but there isn’t any games you can play on the Nintendo or xbox unless you download them I guess and you can’t even put your games into the switch because it is locked up. Also, there was an air hockey table with no puck to play on it. Not a big deal but the kids were very excited for the game room. Regardless my kids still had fun in there and the pool area was very nice. Wasn’t far from the Disney parks so that was great. This community gets very busy with people renting the houses during the weekend. We heard people partying late at night and the roads had cars parked all along both sides so it was hard to get through the neighborhood during the weekend but come Monday it totally cleared out. The house is beautiful and has everything you would need… Thank you again for letting us stay in your lovely home.
Guest favorite
A vibrant game room designed with a Super Mario theme features a red pool table and an arcade-style gaming station. Colorful wall graphics and playful carpet add to the inviting atmosphere. Comfortable gaming chairs are positioned near a desk, creating a fun environment for guests.
Home in Kissimmee
5 out of 5 average rating, 7 reviews

4561 Majestic 9BD Kingdom Retreat Near Disney

SoniaRating, 5 stars1 week ago
Had a beautiful time will definitely rebook with them again
Top guest favorite
A spacious outdoor area features a private pool, inviting lounge chairs, and a submerged spa with views of the serene lake. The pool area is enclosed with a screened canopy, allowing for an abundance of natural light and protection from insects. Lush greenery surrounds the space.
Home in Kissimmee
4.98 out of 5 average rating, 97 reviews

Mickey's Lakefront Villa at Sunset Lakes

MabelRating, 5 stars5 days ago
We didn’t know the gem we were getting h til we walked into this beautiful home. My heart was immediately relieved to see how organized, clean and home like this space was. Our kids were comfortable, my MIL was at ease, it was a great location to get around. My MILK insisted we needed a vacation home of our own, just like this villa. If ever we need to come back to Orlando, we would choose this place again and again.
Superhost
A spacious living area features high ceilings and large windows, allowing natural light to fill the room. Comfortable seating is arranged on a soft area rug, with a cozy gray sofa and stylish wooden chairs. A flat-screen TV is mounted on the wall, enhancing the inviting atmosphere.
Home in Kissimmee
4.8 out of 5 average rating, 5 reviews

Amazing House with Pool & BBQ at Champions Gate

LuisaRating, 5 stars1 week ago
Had a great time! The house is well equipped and the host was very quick to respond when we had questions.
Top guest favorite
A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.
Home in Kissimmee
4.92 out of 5 average rating, 53 reviews

Paradise Suite

TeahRating, 5 stars2 days ago
Just finished up my stay here. It was even better than my expectations. The pool was clean and deeper than I thought it would be. The home was spotless and felt very cozy! Host was very helpful, responsive and welcoming! 10/10 would stay here again and would recommend to anyone!
Guest favorite
The image captures a view from the pool, showcasing the villa's large glass windows and covered outdoor seating area. Loungers are positioned around the pool, offering ample space for relaxation. The sparkling water reflects the modern architecture above, framed by a screened enclosure.
Villa in Kissimmee
4.95 out of 5 average rating, 78 reviews

Private Pool & Free Heat - Close to Disney!

BradRating, 5 stars2 weeks ago
It was a wonderful place! The only issue I have is the host stayed outside in her car for over a hour waiting on my family to leave, made me feel rushed! Check out is at 10 am , she was out there at 9 am !
Superhost
The exterior of a modern two-story house is showcased, featuring a mix of light-colored stucco and stone accents. The front pathway leads to an inviting entrance, with large windows allowing for ample natural light. Lush green grass surrounds the home, enhancing its welcoming appeal.
Home in Kissimmee
5 out of 5 average rating, 3 reviews

X-Magnificent 9BR-Sleeps 23-w/Pool 5mile to Disney

MahoganyRating, 5 stars6 days ago
The home was exactly as described with no problems at check in/out or during our stay. Host was available as needed. I will definitely be rebooking this home for a stay.

Pet-friendly vacation rentals in Kissimmee

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, 114 reviews

Beautiful home. Private pool. Close to Disney!

KrisseyRating, 5 stars2 weeks ago
We had a wonderful stay! Perfect for our family of 7 and our small dogs! Beautiful house and we enjoyed the pool!
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, 131 reviews

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

AmandaRating, 5 stars4 days ago
Our kids and family loved the house ! Pool was nice size that over looked the lake was the best part. It close to Disney about 15-20 mins . House was huge 6 bedrooms and every bedroom had a bathroom . We will hopefully come back again
Superhost
A living room is furnished with a light grey sofa and a matching armchair, offering ample seating. Two coffee tables are positioned centrally on a patterned area rug. Artistic wall decor and warm lighting create a relaxed ambiance, with a dining area visible in the background.
Townhouse in Kissimmee
4.71 out of 5 average rating, 167 reviews

Cozy Townhouse in Kissimmee, near Orlando!

LynnRating, 5 stars2 months ago
Maria's place was super cozy. It had everything we needed and then some. the property is beautiful. Pools were nice. and the staff at the gates were very welcoming. No problems. very relaxing.
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, 103 reviews

Nice pond view home with pool and outdoor theatre!

MichelleRating, 5 stars1 month ago
Came for a birthday vacation and I def chose the right place to stay! The airbnb was close to Disney parks and gift shops. The home was just like the photos, everything was clean and beautiful 😊 The pool was so refreshing and clean, plus had a nice view of the pond. We even decided to stay an extra day, Dinara was super accommodating. I definitely recommend!
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, 411 reviews

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

ShamayaRating, 5 stars2 weeks ago
We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !
Guest favorite
A private south-facing pool is surrounded by a screened enclosure, offering a clear view of the lush conservation area beyond. Poolside lounge chairs are arranged neatly, with tropical plants adding a natural touch to the peaceful outdoor space.
Home in Kissimmee
4.89 out of 5 average rating, 193 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

AustinRating, 5 stars1 month ago
Great stay as always.
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
4.81 out of 5 average rating, 247 reviews

150 Inch 4K Movie Theater Pool & Spa sleeps 16

CarrieRating, 5 stars2 weeks ago
This was a great place to stay. Very clean and felt like home. It was very spacious. We initially had some troubles with the sound of the movie theatre and Sam personally came over to help at 10pm after trouble shooting over the phone didn’t work. Great hosts!
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, 120 reviews

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

DustinRating, 5 stars2 weeks ago
The house was very roomy, peaceful and private. They had everything at the house that a family could need! The resort was also a plus with the water park and other amenities. Having a pool right at the house and being so close to Disney were also a HUGE plus! Our entire group loved the house and loved how we weren’t all crowded on top of each other. The grill on site was also a huge plus as we grilled a few nights while we were there. The host is very responsive and answers messages right away! Would definitely recommend to a family traveling to the area and we will more than likely book again! Thank you!

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 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.

Destinations to explore

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