The city of Kissimmee is the largest in Osceola County, Florida. It was once a lovely ranching town before Orlando’s tourism boom led to its own evolution to draw in all kinds of visitors, thanks to its stunning natural and man-made attractions. Kissimmee Lakefront Park offers walking trails as well as picnic spots for visitors who want to surround themselves with greenery. While you’re here, be sure to visit Monument of States, too. From the park, you can also see Lake Tohopekaliga which is a picturesque body of water where you can go fishing. Old Town, meanwhile, is the place to be if you want to check out the shopping and dining scenes.
These are only some of the places you can see in the city. To give yourself ample time to see the different attractions in the area, read on for the best long-term rentals in Kissimmee, Florida.
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. Spacious house with saltwater pool and game room (from USD 157)
An ideal long-term rental requires amenities such as a full kitchen, laundry facilities, and comfy beds - and this spacious house offers all of these. Plus, it comes with many perks such as a 10% monthly discount.
A saltwater pool and a hot tub provide you with relaxation outlets. You can pay extra to have these heated if you’re in the area during the cooler months. The house also has a game room to stave off boredom while indoors. On-site parking is available here.
2. Newly remodeled condo with access to pool (from USD 85)
Enjoy a nice discount if you book this well-furnished rental for a month or more. This condo is located in a gated community that offers guests shared access to two swimming pools, a fitness center, and tennis courts so you can have an outlet for working out or having fun. There’s also an outdoor play area where you can bring your kids.
The host provides linens and towels for convenience. A starter kit of supplies is also given to welcome you to the unit. Housekeeping services may be provided if needed. Moreover, Disney World is easily accessible from this property.
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
3. Vista Bay Villa (from USD 120)
This renovated villa has been furnished with guests’ comfort in mind. It is well-appointed and includes amenities such as a full kitchen and laundry facilities. A travel crib and a high chair may also be lent for guests traveling with a baby. It also has a private pool which you can have heated for a fee. Loungers are installed there if you want to catch some sun.
The master bedroom is an en suite with a walk-in closet to provide you with ample storage space. What’s more, you can get a monthly discount worth 12% if you book this option.
Top guest reviews
Cleanliness:
the house was very clean and comfortablehouse was nice tile everywhere so it's easy to clean but a little echoeyHost:
owners were very nice and answered promptly with any concerns we had thank youowners were super very easy to get ahold of and very quick response wonderful outdoor area tooRead more reviewsLocation:
it’s also close to many attractionsperfect location for a week of volunteering at give kids the world villageeverything was very comfortable and cozy central location able to deliver groceries and cook there to savegood location close to the parks and a very nice quiet community
4. Renovated waterfront home with pool and game room (from USD 146)
This fully furnished house sits right by a lake, affording you views of the water and the opportunity to go fishing practically any time you want. The rental has its own pool and spa, both of which you can pay to be heated if you’re visiting when it’s cool. The outdoor area is furnished with seats and a table to give you space to hang out.
If you want to stay dry while having fun, you can play in the game room. A crib, a stroller, and a high chair are also available if needed. If you’re planning to stay here for a month or so, you will be eligible for a great discount.
Top guest reviews
Amenities & Room:
the furnishings were very comfortable and even had a plush throw on the couchwe enjoyed the pool spa and the furniture/beds were very comfortablethe living room and dining room were super niceif we had more room to pack more stuff we definitely would have cooked morethe pool was warm the hot tub was nice and relaxingCleanliness:
the house was extremely cleanit was clean with a variety of entertainment optionsthe pool and hot tub were so nice the rooms were nice and clean and very spaciousthe home was clean and well appointedthe house was very clean and communication with the owner was excellentHost:
helpful signs with instructions and directions for trash pool use laundry etc clearly displayed throughout the housethe owner bill is a pleasure to work with and responded quickly to any questions we hadgreat place to stay everything well maintained and owner easily accessible for questionsbill was so nice to work with very responsive especially when we needed himalso the neighbors were very friendly and helpfulRead more reviewsLocation:
the location is goodquiet location peaceful lake and backyardgreat vacation close to a lot nice layoutwas a great location for everything we had planned and needed to dothe neighborhood is welcoming and quiet
5. Exquisite home at a prime location (from USD 145)
Get a 10% discount when you book this charming rental for a long-term stay. This home is located near a couple of top attractions in the area for your convenience. Plus, a manager is on board to address any of your concerns.
The rental itself is well-appointed and beautifully decorated. It has a pool which you can use throughout your stay. It also has a game room so you and your group can entertain yourselves through friendly competition. Video games are also available. This property allows guests to make free phone calls to USA and Canada.
Top guest reviews
Amenities & Room:
beds were sooooo comfortableCleanliness:
the house could use some updates and a deep cleanRead more reviewsLocation:
there was plenty of room for everyone (8 adults) and it was close to everything
6. Oasis Palm Haven (from USD 151)
Oasis Palm Haven has been updated to ensure that it meets guests’ needs. Its kitchen is new and furnished with the essentials so you can prepare a hearty meal with no issues. You can also avail of a discount if you stay here for a month or more.
The yard will truly make you feel that you’re enjoying a holiday in Florida with its palm trees and pool. There’s an outdoor shower there so you can rinse off after a swim. You can also take advantage of the fire pit in that area if you want to sit outside even when it gets dark. Inside, meanwhile, there is a fireplace to give the interiors a romantic touch.
Top guest reviews
Amenities & Room:
we appreciated the good wifi connection and smart tvs around the house as wellthe house even had cute bottles of shampoo conditioner and body wash in each bathroomwe had plenty of room to spread out and the kids enjoyed the poolthe private pool privacy fence and detached guest house were perfect for our familyCleanliness:
very clean and had everything we needed for a relaxing family vacationHost:
the host was responsive when neededwonderful stay the home is updated and has a lot of room to host a large family or twohome is beautiful and very clean the host were amazing and clear with instructions for my arrival and departureRead more reviewsLocation:
the location was great for the local attractionsi would definitely recommend this locationthe location is perfectly nestled in a quiet clean subdivision stores and restaurants are conveniently closethe neighborhood was very nice and quietclean house and close to disney world and universal studios
7. Holiday home in a quiet gated community (from USD 104)
Save up to a whopping 40% if you book this beautiful rental long-term. This house is in a quiet gated community and you are welcome to use the shared facilities here, such as the pool, game room, barbecue grills, play areas, and even a fitness center. The rental is also at a central location, giving you easy access not only to shops and restaurants but also to the top attractions in the area.
Housekeeping services may be provided if needed.
8. Spacious townhouse with child-friendly amenities (from USD 220)
Check out this rental if you’re looking for a place that can comfortably accommodate a big group. This new house is well-located, putting you close to a supermarket, a gas station, restaurants, and other local attractions.
The house is well-appointed for guests’ long-term needs. The host can provide you with a crib and a high chair if you’re traveling with an infant. You can pay extra if you want to use the hot tub and the grill. Moreover, you can also avail of a generous monthly discount.
Top guest reviews
Amenities & Room:
of course the best part was the warm pool in the backyardhowever there is a really nice community pool on the same street as the propertyCleanliness:
everything was very clean and beautifulvery clean and comfortable homesuper clean and full equippedhouse was super clean and the communication was 10/10it was clean and everything seemed well maintainedHost:
the host responds very fast and tries his best to accommodated one’s inquiriesit was nice beside the fact i thought super host have extra trash bags/ tissue etcgreat location host is fast at responding to any questionsour stay here was great cairo is very nice and friendlyclose to the parks very clean excellent hostRead more reviewsLocation:
the place was in a great area close to multiple thingslocation was great cairo was good to work withit is a gated neighborhood which makes you feel secure and it pretty quiet and relaxedgreat place and very close to a lot of supermarkets & food placesthis airbnb is great location is perfect for the theme parks and the house is amazing
9. Blue Haven (from USD 85)
Looking for a pet-friendly property? Check out this rental. The host allows guests to bring their pets provided they are informed beforehand and the corresponding fees are settled. The property is in a quiet neighborhood that nonetheless makes it easy for guests to get to the attractions of Kissimmee and Orlando.
The rental provides guests with linens, towels, and toiletries so they don’t have to worry about packing their own for the trip. Beach gear is also available if you want to spend time in or by the water while in Florida. A great monthly discount is offered by this option.
Top guest reviews
Amenities & Room:
house is beautiful lake view kitchen driveway nice neighbourhood close to disney parksCleanliness:
very clean and comfortable staygreat value for clean convenient stayit was clean and the inside is exactly as the pictures describewe had a great stay it was super clean and very niceher and andy's home is very clean and peacefulRead more reviewsLocation:
close to all attractionsexcellent location very comfortable and near de parksit was close to everything and the neighborhood was peacefulamazing place to create life long memories nothing is more than 30 min of a drivehad a perfect and lovely stay at this location
Superhost
10. Deluxe studio ideal for couples (from USD 69)
This rental is good for two people, making this the perfect option for couples or even solo travelers. A 10% monthly discount also means you can use the funds for your other holiday expenses.
The property gives you easy access to local shops, restaurants, and parks. If you’re flying in, you can arrange with the host to provide airport transfer services for an additional fee. The property also has its own kitchen. Parking for one car is available here as well.
Top guest reviews
Amenities & Room:
the place is roomy for an efficiency with the conveniences of a kitchen and fully functional acthe room was clean and the air condition was super efficientthe bathroom was impeccable which sometimes isn't the case even at nice hotelsluis provides an excellent room for relaxing in with all the basic essentials you'll need for your stayCleanliness:
really clean and quietthe neighbor is quiet clean and safe (gated)very comfy clean and quietthe unit is new very clean and privatethe area is safe and quiet the airbnb itself is very clean and extremely spaciousRead more reviewsHost:
he is a very nice hostthe host luis was very attentive and friendlygreat place and even better hostsluis and julian are friendly and pleasant hostsstay was good host was very nice and helpful
Make the most out of your holiday in Kissimmee
Kissimmee may be known as a good jump-off point to get to Orlando, home of various family-friendly attractions, but the city also has its own set of offerings to its visitors. By booking one of these rentals, you will be able to give yourself time to see these places for yourself.
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