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Vacation rentals in Kissimmee

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Popular amenities for Kissimmee vacation rentals

Stay near Kissimmee's top sights

The Hideaway Club House at Storey Lake5 locals recommend
Kissimmee Lakefront Park171 locals recommend
FantasyWorld Resort7 locals recommend
Silver Spurs Arena9 locals recommend
Walmart Supercenter859 locals recommend
Lake Buena Vista Factory Stores254 locals recommend

Private vacation rentals in Kissimmee

Superhost

Home in Davenport

5 out of 5 average rating, 4 reviews

Villa 4BD in Champions Gate for 8 – Private Pool

JoaquimRating, 5 stars1 month ago
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!
Superhost

Home in Davenport

4.75 out of 5 average rating, 65 reviews

Holiday home

Debra LynneRating, 5 stars2 months ago
Miguel helped us move in quickly after our home was destroyed by Hurricane Milton. He was very responsive to any question or issue.
Superhost

Villa in Davenport

4.88 out of 5 average rating, 8 reviews

Spacious Multi Family Villa- 6Br Sunny Pool Deck!

CaressaRating, 5 stars2 months ago
We enjoyed our stay! The host was accommodating, responsive, and friendly. Clean, spacious, and worth the price. Look forward booking with them again.
Superhost

Home in Kissimmee

4.88 out of 5 average rating, 235 reviews

Private Heated Pool & Hot Tub; 6 miles to Disney

MelanieRating, 5 stars3 days ago
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!
Superhost

Villa in Davenport

4.75 out of 5 average rating, 104 reviews

PRIVATE 5 Bedroom Villa with AMAZING views

WhitneyRating, 5 stars2 months ago
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.
Superhost

Home in Kissimmee

4.88 out of 5 average rating, 183 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

RolandaRating, 5 stars1 month ago
I’ll definitely stay here again!
Superhost

Home in Four Corners

4.86 out of 5 average rating, 43 reviews

H2412T-Windsor at Westside Resort/POOL/Water Park

NorbertoRating, 5 stars2 weeks ago
Very Comfortable Home for my Family. Would definitely consider staying here again the next time we come to the area.
Superhost

Home in Kissimmee

4.7 out of 5 average rating, 142 reviews

THE BEST for Large Families Private Pool & Theater

RhodaRating, 5 stars1 month ago
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

Superhost

Guest suite in Orlando

4.86 out of 5 average rating, 88 reviews

Private Studio, with off-street parking!

MariaRating, 5 stars2 weeks ago
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!
Guest favorite

Townhouse in Orlando

4.98 out of 5 average rating, 80 reviews

Modern 2 story 4/2.5 Convenient Downtown Gem

LauraRating, 5 stars1 month ago
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!
Guest favorite

Home in Kissimmee

4.91 out of 5 average rating, 128 reviews

Guests favorite, Pool, Spa,Game Room, Pets OK

RachelRating, 5 stars2 months ago
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!!
Superhost

Townhouse in Kissimmee

5 out of 5 average rating, 4 reviews

MY HAPPY PLACE 5 Near Celabration and Disney

JulianneRating, 5 starstoday
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.
Superhost

Townhouse in Davenport

4.78 out of 5 average rating, 41 reviews

Fantastic 5BD Pet friendly Home with pool and BBQ!

TieraRating, 5 stars2 months ago
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!
Guest favorite

Apartment in Orlando

4.94 out of 5 average rating, 52 reviews

D&D’s Private Orlando Loft w fenced backyard!

AndrewRating, 5 stars3 days ago
Honestly really nice. Loved the privacy and yard space provided.
Guest favorite

Home in Kissimmee

4.89 out of 5 average rating, 160 reviews

Private pool home close to Disney

BrenoRating, 5 stars1 month ago
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
Superhost

Home in Orlando

4.62 out of 5 average rating, 55 reviews

NEWLY remodeled PET FRIENDLY 2br/1bath by OIA

OlgaRating, 5 stars1 week ago
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

Superhost

Townhouse in Davenport

4.77 out of 5 average rating, 26 reviews

Enchanted Oasis | Private Pool | 12 min to Disney

JorgeRating, 5 stars5 months ago
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!
Guest favorite

Condo in Kissimmee

4.76 out of 5 average rating, 89 reviews

Waterview Condo Close to Disney

JamieRating, 5 stars1 month ago
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
Guest favorite

Home in Davenport

5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

IrynaRating, 5 stars13 months ago
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.
Superhost

Home in Kissimmee

4.68 out of 5 average rating, 22 reviews

Vacation Home with Pool & Spa near Disney

StephanieRating, 5 stars4 months ago
It was very peaceful and a nice house! Thank you
Guest favorite

Condo in Kissimmee

4.9 out of 5 average rating, 116 reviews

D-Gated Resort-5 miles to Disney-2 FREE Water Park

MichaelRating, 5 stars1 month ago
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 :)
Guest favorite

Cabin in Orlando

4.89 out of 5 average rating, 103 reviews

The Moose Cabin, Luxury Stay

KeishlaRating, 5 stars3 weeks ago
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 🙏
Guest favorite

Home in Kissimmee

5 out of 5 average rating, 7 reviews

Lovely home away from home!

ChristaRating, 5 stars1 month ago
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.
Superhost

Home in Four Corners

4.85 out of 5 average rating, 13 reviews

DisneyVacationHomeLazyRiver9021

DominiqueRating, 5 stars2 months ago
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

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