
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

Home w/ PVT Pool, Game Room & Resort access
My whole family loved this house and everything about it. We will definitely stay again on our next trip.

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!

Magical & Cozy Home - Runaway Resort 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.

Beautiful family home near all attractions.
Super attentive and helpful. Very kind. Allowed a late checkout to help me accommodate my changed flight. Comfortable. Felt safe.

Private Heated Pool & Hot Tub; 6 miles to Disney
This is our second time at this house and we enjoyed the space just as much as the first time. Will be coming back again for sure

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi
Another great stay here!

Luxury Pool Home Near Disney
We had an amazing stay, the place was centrally located but out of the hustle and bustle of traffic. We were able to get to Disney and ESPN center fairly fast. The townhouse was much bigger than anticipated. Absolutely would stay here again.

Entire Townhouse -Kissimmee, 4 Bedrooms 3 Bath
Cármen is an excellent host! The house is a grace, very well equipped, the condominium is complete. In addition, it is very close to Disneyland. We love it, we'll definitely be back!
Pet-friendly vacation rentals in Kissimmee

1BD Cottage "Limoncello" in Margaritaville
Daniel’s place was perfect for our excursions to Disney & Universal studios. He was quick to answer with any questions we had & there were a lot of choices of various restaurants in the area.

Mills Lakeside
Great place to stay! Beautiful property, would stay here again.

Modern 3 Bedroom Apartment Near the Theme Parks
Very pleasant and worth the stay! Our host was very responsive and helpful. The area we stayed was also quiet which was also a good thing. Also the location is so close to so many stores, restaurants and parks. I will be visiting again

Pet Friendly Reunion Condo Minutes from Disney!
Amazing little spot if you are in the Orlando area. Pristine air b&b. I walked into a freshly clean condo with soft music playing on the tv, lights turned on and a plate of snack waiting for me. Communication was wonderful and the door was peaceful and homey. Absolutely would stay here again.

Close to Disney!
We had a great stay here, the kids loved the pool, and everything was clean.

Amazing Pet-Friendly 3BR condo near Epic Universe!
The space was perfect for my family. We enjoyed the pool and location was perfect for stores, and near the convention center where my daughter had a competition. Great communication with host was quick to respond.

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

Jas Vacation Home
We had everything we needed and enjoyed our stay. It was the perfect location and setting for our family. The only thing I can suggest is getting the back gate fixed so it latches.

(Discounted Rates) Vacation Home (4 Miles Disney)
Nice place and a great location. The villa is ideal for a lovely holiday to Orlando and in an ideal location with a lake behind and very scenic. Would return again and Jeff is a great host.

Beautiful Gated Home near Disney and Universal
Our stay was great ! Everything was exactly as described. The beds are super comfy and the whole house was clean and tidy. Our host sent clear instructions and our stay was smooth . Would absolutely book again ! Thank you !!

Orlando Home with Private Pool & Game Room !
We had an awesome stay! The house was incredibly spacious. The location was perfect— close to everything including the Disney parks. There are also many food options close by. The kids loved the game room and pool. I would recommend staying in this home.

Modern Home near DT&Airport/Community Pool Nearby
we had a wonderful stay in Orlando house was spacious and only 20 minutes from UCF where our daughter was the house looked just like the photos. very comfortable and lots of towels! everything we needed I kitchen. host was extremely responsive which is important!

New Family friendly townhome.
Very pleasant stay, proactive host and always attentive. To be noted for a future visit.

Spacious 5BR Villa with Pool, Close to Disney Fun!
Stayed here as a family and was lovely, everything you needed and kids loved the pool. The house was clean, kirstie was very responsive to all questions and any issues. Would definitely recommend and use again. Thank you! 😁

Jaw Dropping 5 Bed 4 Bath Home in Hampton Lakes
Awesome place! Absolutely loved our stay! Will definitely go back next time in Florida.
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 490 apartment rentals, over 3,470 house rentals to over 740 villa 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
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