
Vacation rentals in Kissimmee
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Kissimmee
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee

Home in Davenport
5 out of 5 average rating, 4 reviewsVilla 4BD in Champions Gate for 8 – Private Pool
Edney was a fantastic host! He made everything easy with clear and friendly communication, ensuring we had everything we needed for a stress-free stay. The house was amazing – spotless, roomy, and thoughtfully decorated, with every detail carefully considered. It completely surpassed our expectations! We would highly recommend staying here and look forward to coming back someday. Thank you, Edney, for an outstanding experience!

Home in Davenport
4.75 out of 5 average rating, 65 reviewsHoliday home
Miguel helped us move in quickly after our home was destroyed by Hurricane Milton. He was very responsive to any question or issue.

Villa in Davenport
4.88 out of 5 average rating, 8 reviewsSpacious Multi Family Villa- 6Br Sunny Pool Deck!
We enjoyed our stay! The host was accommodating, responsive, and friendly. Clean, spacious, and worth the price. Look forward booking with them again.

Home in Kissimmee
4.88 out of 5 average rating, 235 reviewsPrivate Heated Pool & Hot Tub; 6 miles to Disney
This space had exactly what we needed for our family trip to Orlando. We love that each family had their own private bathroom. The pool was a highlight...and so nice to relax in after a busy day. The neighborhood was great, and the privacy of a Airbnb over a hotel was what we wanted! We will absolutely boom this spot again. Thank you!

Villa in Davenport
4.75 out of 5 average rating, 104 reviewsPRIVATE 5 Bedroom Villa with AMAZING views
We enjoyed our stay here. The first thing we did was check for gators in the pond next to the house. we did see one which was pretty cool. The bedrooms were nice. Although we couldn't get the hot tub to work correctly. the hottub and pool wasn't super cold to get in. Seeing the horses behind us was pretty cool. my 3 year old and 2 year old loved seeing the horses everyday. Location is pretty good. nice and peaceful. I would still give this house a 9.5/10 rating even tho the hot tub didn't work. We went to Daytona Beach and Clearwater Florida both being about a 2 hour drive from the house. Old Town and Disney Springs were easy to get too. We didn't go to Disney World but it's also close by.

Home in Kissimmee
4.88 out of 5 average rating, 183 reviews4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi
I’ll definitely stay here again!

Home in Four Corners
4.86 out of 5 average rating, 43 reviewsH2412T-Windsor at Westside Resort/POOL/Water Park
Very Comfortable Home for my Family. Would definitely consider staying here again the next time we come to the area.

Home in Kissimmee
4.7 out of 5 average rating, 142 reviewsTHE BEST for Large Families Private Pool & Theater
Well to start i would like to say i will definitely rent with them again. I was celebrating new years and my birthday. Everything from the space in the house and on the pool patio was awesome. If you have to travel with toddlers they had lots toys, strollers, high chairs etc...The beds are comfortable you'll have a good night sleep. If you're big on movies and tv then the theater is definitely a big hit for the family Bonnie and Sergio are the best to rent from.
Pet-friendly vacation rentals in Kissimmee

Guest suite in Orlando
4.86 out of 5 average rating, 88 reviewsPrivate Studio, with off-street parking!
Kevin’s place was great! Clean & comfortable, and had everything you could need! The location was close to everything we wanted to do for our weekend. The best part was the yard, my dogs loved it!

Townhouse in Orlando
4.98 out of 5 average rating, 80 reviewsModern 2 story 4/2.5 Convenient Downtown Gem
We loved our stay here. The place was so clean with everything we needed - plenty of space and bedrooms. Kitchen was a great gathering place over dinner for our family. Location is near everything you would need - Target, Starbucks etc. We will definitely be back. Thanks for taking such great care of us!

Home in Kissimmee
4.91 out of 5 average rating, 128 reviewsGuests favorite, Pool, Spa,Game Room, Pets OK
I recently stayed at Yvonne's place and was very impressed! We are from Orlando so we were already familiar with the area but it's a great location if you're going to Disney. My only issue was the cleanliness, but Yvonne was quick to rectify it and everything was fine. highly recommend!!

Townhouse in Kissimmee
5 out of 5 average rating, 4 reviewsMY HAPPY PLACE 5 Near Celabration and Disney
Casa Perfect, in the perfect place, and with a caring host, dear and super quick to respond. The house was very clean, it is welcoming in every detail. All clean, super calm and quiet condominium. Great bath, wonderful beds, new towels. We truly feel welcome and very happy with our choice. When we get back to Orlando, we'll definitely stay in the same place. I recommend this hosting note 1000. Thanks Delmy for all the affection with us on this wonderful trip.

Townhouse in Davenport
4.78 out of 5 average rating, 41 reviewsFantastic 5BD Pet friendly Home with pool and BBQ!
Vanessa’s place was very clean and just as nice as the pictures. Vanessa was always responsive with any questions or concerns during our stay. We needed to extend our trip for a day and Vanessa made that very easy for us to do! I would love to come back and stay here with my family!

Apartment in Orlando
4.94 out of 5 average rating, 52 reviewsD&D’s Private Orlando Loft w fenced backyard!
Honestly really nice. Loved the privacy and yard space provided.

Home in Kissimmee
4.89 out of 5 average rating, 160 reviewsPrivate pool home close to Disney
Sarah’s house was great, have literally nothing to complain about, only good things. House was in fantastic shape with great location. Sarah is a great host, very responsive. I will definitely be coming back

Home in Orlando
4.62 out of 5 average rating, 55 reviewsNEWLY remodeled PET FRIENDLY 2br/1bath by OIA
We really liked being there, it is a very quiet place and the communication with our host was excellent, any inconvenience that was presented to us, he quickly solved it.
Other great vacation rentals in Kissimmee

Townhouse in Davenport
4.77 out of 5 average rating, 26 reviewsEnchanted Oasis | Private Pool | 12 min to Disney
Simply Wow I have stayed at a bunch of nice Airbnb before but Winston and his beautiful place took 1st place. From before checking in with all the detailed instructions made checkin super simple. Any time I text Winston he responded right away and helped out with some request that we had. The kids and us loved the decor of the house and setup with the play area in 2nd floor to watch tv even connected their Xbox and played for hours. The pool wasn’t too big but it was the perfect size for all of us to enjoy it together as a family of 9. I would HIGHLY recommended this house to anyone and would definitely stay here again next time we are in the Orlando area. Thanks again Winston for being a great host!

Condo in Kissimmee
4.76 out of 5 average rating, 89 reviewsWaterview Condo Close to Disney
Wow! Susana is an absolutely amazing host. She is responsive, quick to answer and overall very friendly. The place was just a pictured and described. Absolutely beautiful. My husband and I were camping at Fort Wildnerness for the holidays and rented Susana's place for our family to stay. The condo was only 20 minutes (easy drive) from Fort Wilderness. Our family was impressed and really liked the property. Would definitely try to stay at any of Susana's locations should the occasion arise. Thank you Susana! The Eyrich's

Home in Davenport
5 out of 5 average rating, 5 reviewsNew! Windsor Island Resort with pool by Disney 03
Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.

Home in Kissimmee
4.68 out of 5 average rating, 22 reviewsVacation Home with Pool & Spa near Disney
It was very peaceful and a nice house! Thank you

Condo in Kissimmee
4.9 out of 5 average rating, 116 reviewsD-Gated Resort-5 miles to Disney-2 FREE Water Park
Our first time in Disney was made better because of james apartment made our whole holiday so much more enjoyable:)from been so close to Disney to having a r2d2 cushion that my daughter loved.I can't fault the place in the slightest it had everything you could need and more thank you for making our holiday the best :)

Cabin in Orlando
4.89 out of 5 average rating, 103 reviewsThe Moose Cabin, Luxury Stay
We had a wonderful night staying at this beautiful cabin.The place was spotless and very clean the host was very communicative all the time. thank you jose 🙏

Home in Kissimmee
5 out of 5 average rating, 7 reviewsLovely home away from home!
Great place. Very kid friendly and the layout was perfect. Not too far from Disney properties also. It worked out very well for our group. Resort was nice too. Property managers were very responsive. Overall I would recommend.

Home in Four Corners
4.85 out of 5 average rating, 13 reviewsDisneyVacationHomeLazyRiver9021
Everything was good. We had no problem at all with the place.
Quick stats about vacation rentals in Kissimmee
Total rentals
7.3K properties
Total number of reviews
236K reviews
Family-friendly rentals
6.2K properties are a good fit for families
Pet-friendly rentals
1.2K properties allow pets
Rentals with a pool
6.6K properties have a pool
Rentals with dedicated workspaces
4K 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 790 villa rentals, over 490 apartment rentals to over 3,510 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 4,000 vacation rentals in Kissimmee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Destinations to explore
- Four Corners Vacation rentals
- Orlando Vacation rentals
- Central Florida Vacation rentals
- Saint Johns River Vacation rentals
- Tampa Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Fort Lauderdale Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Miami Vacation rentals
- Florida Keys Vacation rentals
- Family-friendly rentals Kissimmee
- Mansion rentals Kissimmee
- Monthly Rentals Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with breakfast Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a sauna Kissimmee
- Resort rentals Kissimmee
- Rentals with pools Kissimmee
- Cottage rentals Kissimmee
- Villa rentals Kissimmee
- Apartment rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with beach access Kissimmee
- House rentals Kissimmee
- Hotel rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Serviced apartment rentals Kissimmee
- Cabin rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with a home theater Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Condo rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with an accessible height bed Kissimmee
- Rentals with an EV charger Kissimmee
- Tiny house rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Rentals with lake access Kissimmee
- Rentals with a washer and dryer Kissimmee
- Kid-friendly rentals Kissimmee
- Private suite rentals Kissimmee
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Food and drink United States
- Sightseeing United States
- Art and culture United States
- Wellness United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States
- Things to do Florida
- Art and culture Florida
- Wellness Florida
- Entertainment Florida
- Food and drink Florida
- Sightseeing Florida
- Nature and outdoors Florida
- Sports activities Florida
- Things to do Osceola County
- Art and culture Osceola County
- Things to do Kissimmee
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes