Kissimmee vacation rentals
Vacation rentals in Kissimmee — enter your dates to book direct
Kissimmee offers proximity to theme parks and attractions such as Old Town, Lake Tohopekaliga (Lake Toho), and Gatorland. Visitors often venture here for family-friendly fun at Disney World and Universal Studios Orlando. Houfy connects travelers directly with Kissimmee hosts, allowing bookings without intermediaries. Discover a range of properties, from pool homes to resort condos, with access to nearby Celebration and Davenport. Visitors benefit from the Orlando area's attraction-rich landscape and temperate climate nearly year-round.
Explore near Kissimmee
Cities and towns within driving distance of Kissimmee, each bookable direct with the host.
Top-Rated Vacation Homes in Kissimmee
Browse the highest rated vacation properties in Kissimmee.
$1,954.13 USD total for 4 nights
Sep 8 – 12, 2026
The hosts, Zack & Ivy were amazing. They responded quickly and have done such an incredible job on their house. We had a big group and were all beyond happy with the house. The pool, game room and multiple community pools were used thoroughly by us. There was plenty of space for all of us and we will be back to this rental!
$6,110.84 USD total for 3 nights
Sep 8 – 11, 2026
This house was a dream come true!!! We spend two days in the house because it was so much to do! The decorations and attention to detail was flawless! Every room was perfectly themed by a sport. The art for each themed room was impeccable. The glow in the dark carpet was a great addition! The bowling alley is amazing! The pool is huge and I was able to watch tv while swimming! How luxurious!! The arcade was fun! The theater was comfortable! We literally didn’t want to leave the house! Cliff was a ideal host/homeowner! He was responsive to all questions. The house was so high tech, 200 inch tv, 150 inch theater, phone apps to control all electronics, stars ⭐️ in the ceiling and flashing lights, I felt like I was in the future! I’d book this house a million times if I could! Definitely, coming back!
$707.11 USD total for 3 nights
Sep 19 – 22, 2026
Our stay at Rafaela‘s was great! My kids loved the themed rooms, the community pools with the lazy rivers and the pool at the house. The location was good and safe with Target and other shops/restaurants near by. We did a day at Universal and one at Disney and both were easy to get to! Everything in the house was clean, spacious and well maintained! Would recommend to anyone staying in the Orlando area that wants to be near the parks but also have your quiet time. Rafaela was a great communicator and easily accessible. We would stay again!
$656.03 USD total for 3 nights
Sep 8 – 11, 2026
This house was great for our group of 6. The kids loved the theme rooms and the small pool at the house. The community has 2 resort style pools with lots of fun things for kids to do. My son (5) loved the lazy river and the water cannons. The house was very clean and the kitchen was well stocked with everything we needed. Overall, this is a great spot for a trip to Orlando. Easy ride to the theme parks, Target is 5 min away for groceries, the community’s is friendly and safe. Short drive to many different restaurants. Not sure how it could be any better. We will be back again next year.
$611.77 USD total for 3 nights
Sep 8 – 11, 2026
My husband and I truly enjoyed our stay at this beautiful home! It looked exactly like the pictures and felt even better in person. The kids had an amazing time, especially swimming in the pool at night with the cozy string lights such a fun touch! Every room was decorated perfectly with LED lights, which made it feel like home for our kids. The location is super convenient, with plenty of grocery stores, restaurants, and shops nearby. Tip: Google alternate routes to avoid tolls. We also loved having access to two clubhouses — Bronson Clubhouse was just a short walk away and a great bonus. Rafaela was incredibly kind and responsive. I had a special request for my kids, and she made it happen. I officially became the best mom ever thanks to her help! I highly recommend booking this space. Rafaela is a wonderful host, and my family is already planning our return next summer!
$573.18 USD total for 3 nights
Sep 26 – 29, 2026
We thoroughly enjoyed our stay at this unit. It may have been the cleanest vacation rental we have ever rented. The unit was nicely decorated, and if you have young children, they would especially enjoy the Disney themed room. We liked the large TV in the living room, the refrigerator with ice and water on the door, and the king-sized bed. The complex had nice walking areas, and we especially loved the clubhouse area with pools, hot tub, lazy river, and fitness center. It is convenient to shopping and restaurants. Highly recommended!
$572.04 USD total for 3 nights
Sep 11 – 14, 2026
My family and I enjoyed our time staying at Rafaela's house. Her place was very cozy and clean more like spotless!! everything was easy access we had no trouble with anything instructions where very clear and Rafaela was very kind & polite ready to help if we needed anything. Everything is nearby the house stores, restaurants, disney parks , etc...Also the pool and the small Waterpark are a must kids loved it. We hope to comeback soon! Thank you again for a great stay! Definitely recommend!
Lovely Themed 3-BR in resort 10 min from Disney FREE WATERPARK
$539.13 USD total for 3 nights
Sep 8 – 11, 2026
Our family of 6 just returned from a 4 night stay and the only downside was the fact we did not find this place sooner and get to stay all 9 days here!! The property is exactly as shown in the photos, beds are comfortable and the space is very clean. Rafaela was very acomodating and responsive. We enjoyed morning coffee on the large deck overlooking the pond. The building is quiet and we never heard anything from the surrounding units. The on site water park makes you feel like you are at a resort and was perfect for our "down-day." We would 100% return to this property.
Recommended Homes in Kissimmee
Handpicked properties we think you'll love in Kissimmee.
$474.68 USD $459.35 USD total for 3 nights
Sep 8 – 11, 2026
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$1,823.08 USD $1,689.57 USD total for 4 nights
Sep 14 – 18, 2026
$1,495.85 USD total for 7 nights
Sep 8 – 15, 2026
$792.90 USD total for 6 nights
Sep 10 – 16, 2026
$1,565.00 USD total for 3 nights
Sep 8 – 11, 2026
$1,163.38 USD total for 5 nights
Sep 8 – 13, 2026
Vacation houses with pools in Kissimmee
Cool off in style with these amazing pool homes in Kissimmee.
$5,186.95 USD total for 5 nights
Sep 8 – 13, 2026
$6,110.84 USD total for 3 nights
Sep 16 – 19, 2026
$1,126.29 USD total for 3 nights
Sep 14 – 17, 2026
$514.16 USD total for 3 nights
Sep 9 – 12, 2026
Elegant Blue Moon House - TOP Stay 10 Minutes from Disney
$548.21 USD total for 3 nights
Sep 9 – 12, 2026
Pet friendly vacation rentals in Kissimmee
Bring your furry friend along! Browse pet-welcoming homes in Kissimmee.
$532.56 USD total for 3 nights
Sep 8 – 11, 2026
$517.56 USD total for 3 nights
Sep 10 – 13, 2026
3121-406 · Stylish Apartment with Privilage Location & View
$526.76 USD total for 3 nights
Sep 8 – 11, 2026
Enchanting Orlando Getaway: Luxurious Private Pool Home Near Disney
$642.41 USD total for 3 nights
Sep 8 – 11, 2026
$517.56 USD total for 3 nights
Sep 8 – 11, 2026
Why visit Kissimmee
Discover what makes Kissimmee a perfect vacation rental destination.
Must-Visit Theme Parks
Proximity to Walt Disney World
Kissimmee is just a 15-minute drive from Walt Disney World Resort. Experience thrilling rides and magical attractions practically in your backyard.
Premium Outlet Malls
Deals just 10 miles away
Shop designer brands at Orlando Vineland Premium Outlets, located only 10 miles north of Kissimmee. Enjoy discounts on top labels and brands.
Explore Shingle Creek
Scenic nature trails nearby
Hike or kayak along the Shingle Creek Regional Park trails, a natural escape located just 6 miles from downtown Kissimmee.
Perfect for Family Fun
Family attractions year-round
Enjoy attractions like Fun Spot America with go-karts and roller coasters. It's less than 5 miles from central Kissimmee.
Where to stay in Kissimmee
The best areas and neighborhoods for your vacation rental in Kissimmee.
Celebration
Originally developed by Disney, Celebration features charming streets and picturesque lakes. Enjoy community events and a friendly atmosphere.
Downtown Kissimmee
Offers a blend of old Florida charm with modern amenities. Short walk to restaurants, parks, and the Kissimmee Lakefront Park.
Osceola Parkway
Convenient access to attractions and theme parks. Ideal for shopping and dining with numerous outlets along the route.
Poinciana
Located a bit farther from the tourist hustle, Poinciana offers affordable accommodations and a quiet residential feel.
Find Kissimmee vacation rentals that suit your style
Vacation homes, condos, villas and more — pick the kind of Kissimmee vacation rental you want, then book it direct with the host.
Kissimmee vacation rentals with free WiFi, hot tub or air conditioning
Free WiFi, hot tub, air conditioning and more — every Kissimmee vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Kissimmee
All within driving distance of Kissimmee vacation rentals.
Walt Disney World Resort
A world-renowned theme park only a short drive from Kissimmee. · 15 miles
Universal Studios Florida
Experience movie-themed rides and attractions at Universal, located north of Kissimmee. · 17 miles
Gatorland
Visit the 'Alligator Capital of the World' with more than 2,000 alligators and crocodiles. · 8 miles
Osceola County Historical Society Pioneer Village
Explore an authentic pioneer village showcasing life in the 19th century. · 9 miles
Shingle Creek Regional Park
Enjoy hiking trails and kayaking in a serene natural setting. · 6 miles
Orlando Vineland Premium Outlets
Shop for your favorite brands at discounted prices. · 10 miles
Best Time to Visit Kissimmee
Kissimmee has a subtropical climate with hot, humid summers and mild winters. Best months to visit are November to April with temps ranging 50-80°F.
| Month | Avg High | Rainfall | Demand |
|---|---|---|---|
| JanJanuary | 71°F | Low | Mid |
| FebFebruary | 74°F | Low | Mid |
| MarMarch | 78°F | Moderate | Peak |
| AprApril | 83°F | Moderate | Peak |
| MayMay | 88°F | Moderate | Mid |
| JunJune | 91°F | High | Low |
| JulJuly | 92°F | High | Low |
| AugAugust | 91°F | High | Low |
| SepSeptember | 89°F | High | Low |
| OctOctober | 84°F | Moderate | Mid |
| NovNovember | 78°F | Low | Mid |
| DecDecember | 73°F | Low | Mid |
Getting to and around Kissimmee
Kissimmee is easily accessible by car, with nearby airport and transit options for visitors.
- ORLANDO INTERNATIONAL AIRPORT
- Located 18 miles away, this major airport offers numerous domestic and international flights.
- CAR RENTAL OPTIONS
- Numerous car rental companies are available at the airport and around the city for easy exploration.
- LYNX BUS SERVICE
- Local buses link Kissimmee with surrounding areas, providing a convenient travel option.
Similar vacation rentals near Kissimmee
Homes within 60 miles of Kissimmee, from verified hosts.
$816.07 USD total for 4 nights
Sep 8 – 12, 2026
$1,434.64 USD total for 4 nights
Sep 27 – Oct 1, 2026
$924.74 USD total for 3 nights
Sep 8 – 11, 2026
$1,257.42 USD total for 7 nights
Nov 21 – 28, 2026
$910.50 USD total for 4 nights
Sep 8 – 12, 2026
$1,850.05 USD $1,691.60 USD total for 4 nights
Sep 14 – 18, 2026
Direct with the host
Message the host before you book. Ask questions, confirm details, and deal with the person who owns the property.
Verified hosts
Every host completes identity verification before a listing goes live.
Itemised pricing
Every charge is shown before you pay — including the API connection fee, where one applies.
Explore destinations around Kissimmee
Frequently asked questions
Quick answers about booking vacation rentals in Kissimmee and what direct booking on Houfy actually means.
Visit Kissimmee between November and April for pleasant weather and fewer tourists. Temperatures are comfortable, making theme park visits enjoyable.
Yes, many rentals in Kissimmee welcome pets. Filter your search on Houfy to specify pet-friendly options for your stay.
Stay in Celebration for a charming experience, or choose Osceola Parkway for easy park access. Downtown Kissimmee offers a local vibe.
Vacation rentals in Kissimmee range from $80 to $300 per night, depending on location, size, and amenities. Rentals offer various options for different budgets.
Vacation rentals often provide more space and amenities like a full kitchen, making them ideal for families or longer stays compared to hotels.
Kissimmee offers a variety of rentals including condos, single-family homes, and villas. Options with pools or proximity to parks are popular.
Kissimmee is approximately 18 miles from Orlando International Airport, making it a convenient choice for travelers flying in.
Houfy is a direct booking platform where travelers contact homeowners directly. It allows guests to pay the listed price directly.
Yes, Houfy is a trusted platform for booking vacation rentals, offering secure communication and payment methods directly with property owners.
























































































































































































































