
Vacation rentals in Kissimmee
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Top-rated vacation rentals in Kissimmee
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Popular amenities for Kissimmee vacation rentals
Private vacation rentals in Kissimmee

Villa 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!

Cute Vacation Home Very Close to Disney
We really enjoyed the house and pool. It was very convenient to parks and shopping /restaurants.

Dream vacation, near Disney
What an incredible stay we had at Rosario's place! We even extended 2 extra nights. Rosario was responsive, helpful, and so kind - she even left a birthday balloon and some treats for my mom's birthday! The house was impeccable and they were great about everything, from changing dates to heating the pool, and keeping it clean, and the pool was a perfect balmy respite. The next time we're in town (and we will be, this is our old neighborhood!), we will definitely try to book here again. Can't wait to come back!

Vacation home
Me and my Family enjoyed our days there! Miguel was very friendly and nice and welcome us to a little welcome gift I mean who dosen’t love chocolate

Nice & Cozy Home near Disney
Everything was excellent! Especially the host's attention, she is ready to help, she responds quickly. It is close to Disney parks, supermarket, restaurants, gas station.

Private Heated Pool & Hot Tub; 6 miles to Disney
Bobbie was super helpful and responded quickly! The hot tub and pool were great and the Mickey motif was perfect! We had a great time and plenty of room. The pool table and pop a shot were an added bonus for the evenings after Disney and Universal! Great time and a great price! Thank you, Bobbie!

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi
Great house and host was very friendly with clear instructions on check in and check out. Pool was clean and well maintained.

H2412T-Windsor at Westside Resort/POOL/Water Park
Very nice place my family and I enjoyed staying at Michael’s place, the only thing I dislike was the fact that is too close to the Disney parks and coming back to the place after being out the traffic is kind of heavy but there is nothing anyone can do about that, Love the place!! Thank you Michael!!.
Pet-friendly vacation rentals in Kissimmee

Disney Playhouse, Private Pool & Spa, Near Disney
We had a great spring break trip here! My boys loved the pool and game room! Well worth the money! Location was great close to food, shopping and Disney! Highly recommend this place for families! The hosts are super helpful and friendly!

MY HAPPY PLACE 5 Near Celabration and Disney
Love the place, felt right at home. Wish we had more private access to the pool like if it was in the backyard but overall the place was lovely. Love that everyone has their own space and bathroom. She was very responsive. Although was very dry in her responses she definitely answered everything very proactive. Would Definitely stay there again.

Modern 3 Bedroom Apartment Near the Theme Parks
I recommend this place. It was easy to find, easy check-in. Host always responsed to my texts, even the silly ones :) The apartment is specious. It was very clean and had lots of towels.

Close to Disney!
Sarah was a very engaging and responsive host. My family enjoyed the place, the kids loved playing pool and swimming in the pool. Would definitely recommend

Westgate Resort/Water Park Onsite Included
Octavia was wonderful. She was always responsive. We loved our room and our stay.

Family Disney Universal Orlando
Host was responsive all the time, she made me and my family feel like home, the place was very clean and accessible, address was clear and she helped me with everything, hope I can visit this place again soon !!

NEWLY 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.

Southwest facing pool! 5 Miles from Disney.
Everything was great! We had a few glitches, but the host was very quick to sort them out. The only thing I think the host needs to change is the heating of the pool, sometimes when we were late getting back from the city, we wanted to get into the jacuzzi after 9 p.m., because the heating of the pool was from 9 a.m. to 9 p.m.
Homes in Kissimmee

(Discounted Rates) Vacation Home (4 Miles Disney)
We had such an enjoyable time here. We highly recommend it to all. The pool was a huge winner for our kids and the location was perfect. Thanks again!

Beautiful Gated Home near Disney and Universal
My stay was amazing I will be booking again

Orlando Home with Private Pool & Game Room !
This was the perfect place to stay for our family vacation. The kids loved the game room and the pool. The house was clean and in a nice, safe neighborhood. Our host was very polite and very responsive. We loved every minute of our stay and we would definitely stay here again. Highly recommend!!

New Family friendly townhome.
Very nice stay, proactive host and always attentive. To keep in mind for a future visit.

There is no other place you want to be than here.
We’ve just finished a fantastic family holiday at this villa and can’t recommend it highly enough. The house was spotless on arrival, with plenty of fresh towels and hotel‑quality linen. The open‑plan living area is bright and welcoming, and the kitchen has every utensil you could possibly need—including a decent sharp knife (rare in rentals!). The private pool is the real star: perfectly clean, comfortably heated, and enclosed for peace of mind with younger children. Location‑wise, it’s an easy drive to Disney and Universal, but far enough away to escape the crowds; supermarkets and restaurants are only a few minutes up the road. Communication with Frank was first‑class from booking to check‑out—quick replies and genuinely helpful advice. If you’re after a stress‑free, family‑friendly base in the Orlando area, book this place—you won’t be disappointed.

Spacious 5BR Villa with Pool, Close to Disney Fun!
This is overall a nice place in a gated community. The home is large and the amenities are great. A short 2 block walk to the community center pool with small waterpark was also really nice especially for kids.

Jaw Dropping 5 Bed 4 Bath Home in Hampton Lakes
Luis was a very responsive host, we had small issues throughout 8 week stay and he always replied quickly and got things handled. A large part of our time there included us having our 88 year old mother with us and it was very satisfying to have Luis follow through on his promises for the pool heat level and air conditioning level at night so she could sleep comfortably. The house suited our family very well with 5 bedrooms and 4 washrooms, 3 of the bedrooms included ensuites. The pool was part of the highlight with sun shining usually from 11am to 6pm. Overall we were quite satisfied with our choice

Family Home Gated 10 Beds Pool Disney 7 miles.
Great stay! The place was clean, comfortable, and exactly as described. Roy was very responsive and made check-in super easy. Would definitely recommend and stay again!
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 3,470 house rentals, over 740 villa rentals to over 490 apartment 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
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- Cocoa Beach Pier
- ESPN Wide World of Sports
- Universal Orlando Resort
- Reunion West
- Amway Center
- Kissimmee Lakefront Park
- ChampionsGate Golf Club
- Epcot
- Disney's Hollywood Studios
- Universal's Islands of Adventure
- Blue Spring State Park
- Magic Kingdom Park
- Aquatica
- ICON Park
- Island H2O Water Park
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