Kissimmee in the state of Florida is known for a plethora of attractions for tourists. To get to know the local culture and history, visit Osceola County Welcome Center and History Museum. If you prefer artsy activities, visit The Osceola Performing Arts Center known for its Broadway-style and avant-garde shows. Want to try something new? Then visit Silver Spurs Arena during the historical rodeo to see the cowboys ride or participate in rodeo parades. Tourists here can also meet crocodiles in their natural habitat. Enjoy watching the alligators while taking an airboat ride on Lake Tohopekaliga, about 30 minutes away from the city. If you want to do justice to all this city has to offer, you must plan an extended vacation. Check out our list of the best monthly rentals in Kissimmee, Florida, to ensure a hassle-free and budget-friendly trip.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Renovated apartment with pools (from USD 85)
If you’re traveling with your kids, this condo located just 7 miles (11 kilometers) from Walt Disney World® Resort, is perfect for you. There is a workplace in the house for guests who need to attend meetings and work on assignments. At the end of the day, you have the opportunity to relax on a cozy porch with a cup of coffee. Additional amenities include two pools and tennis courts.
A 5% rental discount awaits if you rent the condo for 28 nights or more.
Top guest reviews
Amenities & Room:
we had a very comfortable stayCleanliness:
the apartment was clean and tidy on arrivalit was clean comfy and a great place for 2everything was nice and cleanclean quiet and within 15 minutes of universal and disneyspacious and clean and quiet close to familyRead more reviewsLocation:
overall the complex was a nice place and very family-friendly
2. The Grand Palm (from USD 190)
This spacious home, located in the heart of Kissimmee, is the perfect choice for a large family. You can have fun playing darts, air hockey, and other games available in this place. Or, organize a fun barbecue evening on the furnished patio.
You can also prepare more elaborate meals in the spacious and fully equipped kitchen. Rent this house for 28 nights and get a monthly discount of 13%.
Top guest reviews
Read more reviewsHost:
we really enjoyed our stay the place was very clean and the host was exceptional
3. The Compass Cottage (from USD 75)
If you’re looking for a vacation rental in a quiet area near Walt Disney World® Resort and Lake Tohopekaliga, then you will love this cottage. Here, you can enjoy leisurely conversations while strolling in the lovely garden.
In the evening, you can sit with the whole family on a plush sofa to watch a movie on the HDTV. Or, after a day of sightseeing, come back to relax in a fully equipped bathroom with a bathtub and shower. Save 10% of the rental price by booking this cottage for a month.
4. Luxury townhouse in Venetian Bay Villages (from USD 122)
This stylish two-story townhouse is close to major attractions and shopping places. Its elegance is enhanced by the exterior of the house with neat white fences and beautiful lawns.
In the evening, sit in a cozy corner on the sofa and spend time in silence while reading a book. At the end of the day, retire to the bedrooms furnished with king- and queen-size beds. Save 10% by booking this property for at least 28 nights.
Top guest reviews
Amenities & Room:
walk to beautiful facilities pool(at 86 deg) hot tub exercise room and club housenice amenities exercise room arcade bingo pot luck dinners and very friendly staffCleanliness:
it was very clean and adorableit was a very nice place clean and plenty of roomthe place was very clean and we had a great timelet me start by saying this unit smelled super cleanvenetian bay is top notch clean attractive quiet and secureHost:
easy contact with ownerthere were several residents with dogs in the community and all the people were very friendlypatti was very helpful and responsive through the entire processRead more reviewsLocation:
close to restaurants and attractionspool was great and is located right across the streetso relaxing and close to shopping good places to eat and entertainmentgreat place to stay atgreat location large condo with all amenities
5. Fully air-conditioned property at Venetian Bay Villages (from USD 84)
This townhouse is perfect for families with kids as there are three playgrounds. Meanwhile, adults can work out in the shared gym and play tennis.
At the end of the day, you can unwind by swimming in one of the pools on the premises. To get a good deal, book this house for a month. In this case, you will get a 30% discount on the entire fee.
Top guest reviews
Amenities & Room:
there was nothing wrong with the community pool itselfHost:
owners and property manager were great to deal with and very helpfulRead more reviewsLocation:
we had a great family vacation just the place needed updating
6. Bright vacation rental with a gym and spa
If you love shopping and dining out, this stylish townhouse near Walt Disney World® Resort is a perfect choice. The open-plan living space with a well-lit lounging area combined with a dining space and a fully equipped kitchen is perfect for enjoying quality time with your family.
The workspace along with complimentary Wi-Fi will allow you to focus. In the evening, go for a workout in the gym or enjoy a treatment in the spa. Staying here for a month can save you 10% on the rent.
Kissimmee, Florida, United StatesAccommodates: 9
Top guest reviews
Amenities & Room:
pools were an added bonus and i got to take my dog along which was perfectwe couldn’t use the tv because it wasn’t a smart tvCleanliness:
the unit is clean and a lot of sleep spaceHost:
daniel was a wonderful hostmy friend and i had a great stay here they’re very kind and respond quicklyRead more reviewsLocation:
the location was great and close to disneythe location was perfect for our triptownhouse was is a good location near shoppinggood location and convenient if you are visiting theme parkssuch an amazing listing it had a ton of room and was very close to everything
7. Stylish accommodation in Cypress Ridge Townhomes
If you’re looking for spacious accommodation close to the attractions in the area, then opt for this two-story townhouse located about a 25-minute drive away from the airport and downtown Orlando.
Start your day with a cup of aromatic coffee prepared in the fully equipped kitchen. At your disposal will be bedrooms, with king- and queen-size beds, and a roomy sitting area with a TV. You will get a 10% discount if you reserve this house for at least 28 nights.
Kissimmee, Florida, United StatesAccommodates: 6
Top guest reviews
Amenities & Room:
we were so comfortable i didn’t want to leavethe living room was quite spacious and perfect for our movie nightCleanliness:
everything was clean and smelled amazinghouse was clean and clear communication from the hostthe unit was very nice clean and spaciousit was very neat and clean lots of roomthe house was amazing everything was clean everything was impeccableHost:
fabulous hospitality from our hosthost was very communicative and has great customer servicebenjo has one of a kind personalized servicegreat host and i definitely recommend staying herebenjo is also very kind he kept in contact with me to make sure everything was okayRead more reviewsLocation:
the airbnb is also in an ideal location with easy access to shopping centers and attractionsi highly recommend this place its close to everything and is located in a quiet beautiful gated communitygreat home perfect location and benjo is the bestplace was definitely worth the 4 hour drivei love your place and will definitely be booking with you again
8. Modern apartment with a shared hot tub (from USD 94)
Take a closer look at this apartment in a gated community with enough space for large families or groups to relax. In the morning, step into the fully equipped kitchen and enjoy a delectable breakfast on the kitchen bar. Then let yourself relax in one of the resort’s pools or soak in the hot tub while watching the beautiful sunset.
At night, book lovers can recline on one of the queen-size beds with reading lights on both sides and enjoy the latest page-turner. Consider staying here for a month and getting a 10% discount.
Top guest reviews
Amenities & Room:
our toddler loved the mickey & minnie mouse roomthe community has a fantastic pool and hot tub as wellCleanliness:
clean and spaciousclean spacious and extremely convenientvery nice clean place great neighborhood and good communicationthe house was nice and cleanthe house is cleanHost:
friendly neighbors and staffgabriel was an amazing hostgabriel was a fantastic hostwe had a great stay and the host was very accommodatingowner is nice and easy to communicate and instructions is clear and usefulRead more reviewsLocation:
close to disney springs and the vineland outlets for good shoppinggreat location comfortable accommodationsgreat location close to attractions stores and restaurantsthe location is excellent close to shops and disneygreat place to stay close to everything and super convenient
Superhost
Enjoy a relaxed vacation in Kissimmee
Kissimmee has a large number of attractions that you will want to visit at your own pace. After a day filled with excitement, let yourself relax in one of the properties mentioned above while making sure that you don’t have to worry about your budget!
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