
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

Gorgeous 5BR @Encore next to Disney - 7710
This home is great, nicely kept and has enough space for everyone with the bedrooms well appointed and 3 king beds - hard to find with AirBnb, most have multiple beds trying to maximize their space, but this place is perfect with a bathroom for each room and privacy in the backyard. Amazing heated pool and jacuzzi and kid and dog friendly! Definitely worth the money, great location and everything you need. Thanks Frank! 💫

4561 Majestic 9BD Kingdom Retreat Near Disney
BOOK IT! The home looks exactly like pictures. It was plenty room for my family and the kids was so entertained with ball pits, slide, pool and game room that we didn’t have to leave the house for entertainment. I love that it was plenty unlimited parking unlike other places I booked. They had a lots of dishes, glasses and utensils available also. They had fast responses and handled all request in a timely fashion. The pool heater was set to perfect temperature. I request it to be set 70 degrees and someone came out and adjusted quickly. My family and I will 100% be back!

Sweet vacation home.
It was an extremely nice getaway, felt like a home away from home! They were very responsive and helpful. Couldn’t have been better!!

Short Drive to Disney Pool + Spa
Osiris responded quickly. The house is just like the photos, very beautiful and with plenty of space, the pool is at the perfect temperature and it is close to Walmart , near to Disney park. I recommend it!!

Amazing Pool, Large, Clean & Private Home, by Anel
We really enjoyed this house. It was very clean and the pool and privacy with the fenced in yard was really nice!

NEW* Water View * Heated Pool * near Disney
From the moment we arrived, we felt completely at home. The space was exactly as described, immaculately clean, beautifully decorated, and full of thoughtful touches that made our stay extra special. The host was incredibly welcoming and responsive, providing clear instructions and always available if and when required. The location was perfect quiet and peaceful, yet close enough to explore everything the area has to offer. Whether we were relaxing indoors or enjoying the nearby attractions, everything about this stay exceeded our expectations. We would absolutely stay here again and highly recommend it to anyone looking for a cozy, comfortable, and memorable Airbnb experience. Thank you for such a wonderful visit!

NEW Luxury Reunion Resort Home |Arcades|Theme Room
I had a wonderful stay in this home. Everything was beautiful and exactly, if not better, than described. Would definitely stay again! 10 out of 10!

10 Minutes to Disney - King Bed, BBQ, Pool, Arcade
Mike’s place was outstanding and so was the location, We were near Disney and other places. I had a concern and he solved it immediately. The house is very nice. One thing I liked was that we were a party of 10 , with 3 full bathrooms everyone was happy. The play room was perfect for the big and small. We had a very good time and definitely if I should go back to Kissimmee I will stay at Mike’s place. Thank you Mike.
Homes for rent in Kissimmee

Blissful Pool Villa • Bears Den • 6mi to Disney
Absolutely hands down the best rental and hosts I’ve ever experienced. The location was close to everything and great area to walk the pups. The house was very clean and spacious. These hosts go above and beyond to make sure your stay is enjoyable and have everything you need. I will definitely be back when I’m in the area again ⭐️⭐️⭐️⭐️⭐️

Stylish 3BR South Heated Pool Just 8 mi to Disney!
Great place to stay, the pool is a big plus. The rest of the house is fine, but don’t expect anything special.

Vacation Home from the Vacation 15 min from Disney
Very beautiful Air bnb with a beautiful lake view , Ricardo was an amazing host

Watersedge of Indian Wells Private Pool & Spa
5 stars - 10/10 Excellent location. So close to everything. Busy surrounding roads but we only ever waited one light cycle at nearby crossroads, which is what causes the traffic. A bit of TLC needed. Scuff marks on walls etc but absolutely nothing that will change the quality of your stay / vacation. Great Pool, a few cracks etc but this doesn’t impact the stay at all. Everyone has a solid wood fence around their pools. Therefore not overlooked and good privacy when swimming. The photos don’t do the villa justice. It’s much better. TV’s are all modern flat screens with streaming capabilities. Bedrooms have curtains - not just blinds as shown in the photos. Appliances are immaculate and fully functioning. We had no issues with ants. No issues with cleanliness. It was a peaceful neighbourhood. We would be more than happy to stay here again, and hope we will. Thank you

7BR Stunning Resort by Disney-Private Pool+Hot Tub
Anne is an outstanding host. Very responsive and her description of the home is spot on! It is a fabulous home that is well appointed and comfortable. Great for families. I would gladly come back. This is truly one of the very best Airbnb’s I have stayed in.

Newly Upgraded 6 Bedroom Dream Near Disney
we had a blast. plenty of space for cheerleaders to get ready in

Heated Pool 15 Minutes to Disney PS5 l Switch
A home away from home when visiting Orlando/Kissimmee! The house had plenty of space, it was close in proximity to all of the Orlando attractions, the pool was amazing, and Brian was a top-notch host! Will definitely stay here again!

Brand New Themed House w Pvt GameRoom&Pool 2159871
Very nice home. My children enjoyed the theme rooms and pool. We will use them again.
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
We had a wonderful experience at Paul's residence. We were in 12. We only used 5 of the 6 suites. The kids loved the game room and the movie theater. They played a lot in the pool. The kitchen has an island where we could dine and talk about how the day had been in the Disney parks. The condominium has a prime location, with a Walmart next door and is less than 30 minutes from Disney and Universal Studios. Paul was very careful, always responding to our messages. The house is really a find. The kids loved it and already want to go back. Thank you again, Paul. Greetings from Brazil.

OMG! Disney Area, Movie Theater, Game Room & Pool!
Our stay was fabulous! The house was just as described. Plenty of room for everyone. We enjoyed the pool, used it everyday! We did not end up heating it, which worked out perfect. The temps were so warm during the day and the sun is on the back of the house all day which is great for being out there. The game/movie room was great and kids loved playing and watching movies. Kitchen had what we needed and we cooked all of our dinners there. Fresh crab legs and ahi tuna near by that was great. It is definitely a place we would return to. Thank you so much for sharing your fabulous place for our family to enjoy for the week!!

House near Disney-Universal w/pool, game room @EV…
Our family had a wonderful stay at Ana’s property. The house was just what we needed for our family of four. The pool was a highlight! Ana was incredibly responsive and we felt right at home. The house is about 20 minutes to Disney and 35 minutes to Universal. My only tiny complaint was that the WiFi was very slow and spotty, but not a huge deal. Otherwise, I would highly recommend this house to anyone traveling to the Orlando area!

Luxury 8Br/6Ba Villa! ! Resort-Pool-Near Disney
My group felt right at home staying at Ying's place. He had everything that we needed and more! Lol The house was clean and looks exactly like the pictures. I would be happy to book this home, with Ying being the host, ANYTIME! Ying is an exceptional host!! His communication is TOP TIER! Ying went above and beyond, and made certain accomodations for us when he didn't have too..... THANK YOU YING! 🥹 You are truly a God send. 😁 If you are looking for a nice, spacious house with an incredible host.... look no further.🗣 BOOK THIS HOME!!! Lol ✌🏽

Free heated 1st night spa/private pool/min Disney
The place was beyond expectations. Everything was great. Accommodations were extraordinary. I have 0 complaints about this place. I would love to stay there again. I will definitely recommend anyone. As soon as you walk into the house. It smells wonderful, fresh, clean. All the commendations for cooking, we're provided, the swimming pool was clean an inviting. Job, well, done for our host. Thank you so much for letting me stay in your lovely place.

*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!

Lakeside Retreat with pool / spa and arcade games
Our stay was excellent! The house had all the features as listed. I would definitely consider this property for future family trips. The game room was awesome, and the heated pool and jacuzzi were perfect!
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, over 460 condo rentals, over 3,470 house 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
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- SeaWorld Orlando
- Universal Orlando Resort
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Reunion West
- Epcot
- Magic Kingdom Park
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- Aquatica
- Disney's Hollywood Studios
- Universal's Islands of Adventure
- Island H2O Water Park
- Blue Spring State Park
- Walt Disney World Resort Golf
- ICON Park
- Universal CityWalk