
Vacation rentals in Kissimmee
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House rentals in Kissimmee

Disney Orlando vacation home with private pool 2
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.

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

Escape to Sun~Kissed Paradise
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!

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

8993-WW 5 Bedroom ALL Suites Pool Home
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!

Dream Villa W/ Pool Near Disney
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.

Pool Home! 10 Min from Disney
So happy with our stay, met our needs completely. Beautiful space, great amenities. We really hope to return, Thank you so much

Stunning and modern 4 bedroom home with pool
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

Cozy 4 bedroom home with pool -Close to everything
Host was responsive! Nicely decorated! Clean!

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

4561 Majestic 9BD Kingdom Retreat Near Disney
Had a beautiful time will definitely rebook with them again

Mickey's Lakefront Villa at Sunset Lakes
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.

Amazing House with Pool & BBQ at Champions Gate
Had a great time! The house is well equipped and the host was very quick to respond when we had questions.

Paradise Suite
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!

Private Pool & Free Heat - Close to Disney!
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 !

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

Beautiful home. Private pool. Close to Disney!
We had a wonderful stay! Perfect for our family of 7 and our small dogs! Beautiful house and we enjoyed the pool!

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

Cozy Townhouse in Kissimmee, near Orlando!
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.

Nice pond view home with pool and outdoor theatre!
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!

OMG! Disney Area, Movie Theater, Game Room & Pool!
We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi
Great stay as always.

150 Inch 4K Movie Theater Pool & Spa sleeps 16
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!

*Brand New!* Minutes to Disney + Free Resort!
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.
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park
- ICON Park
- Universal CityWalk
- Universal's Islands of Adventure