Kissimmee, a city in the state of Florida, stands on the shore of Lake Tohopekaliga. Once largely dependent on cattle ranching, today it’s a popular tourist destination. Famous theme parks such as Walt Disney World® Resort, Universal Orlando Resort, LEGOLAND® Florida Resort and SeaWorld Orlando are within an hour’s drive from here. Kissimmee is home to budget-friendly accommodations that travellers prefer over Orlando’s expensive stay options. However, the city’s pedestrianized Old Town is equally interesting to visit. You’ll find plenty of charming little shops and live entertainment here that will make for a fun day outdoors. There are several rental options in Kissimmee, where you will find rest and relaxation. Nothing beats a calming dip in a pool at the end of an eventful day. Scroll down to read about the best villas with private pool in Kissimmee, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.
1. Fully furnished house near major attractions (from USD 204)
Book this home if you want to stay near Orlando’s main attractions. This place is within a 25-minute drive from several major tourist attractions in Orlando, plus it is the perfect base to relax after all the activity.
Lounging by the pool and soaking in the sunshine is one option or you can plunge into the pool for a refreshing swim session. The pool can be heated for additional fees, so you can enjoy a soothing dip as well. You can prepare a full-fledged meal and dine indoors, or consider paying an extra fee to fire up the barbecue to savour your meal alfresco.
Top guest reviews
Amenities & Room:
eric was a great communicator and the pool was perfectthe temperature of the pool was perfect for those cool eveningsCleanliness:
the house is very clean and spaciousit is very clean house with vey amazing touchthe house was very clean and had everything we neededthe house was clean and the kids really enjoyed the poolme and my family enjoy our stay at this wonderful spot this place was spacious and cleanHost:
eric is a great hosteric was an amazing host he went above and beyond to make our stay one to rememberi throughly enjoyed my visit and eric was a wonderful hostthank you eric for hosting useric was timely and kind in his responsesRead more reviewsLocation:
very close to so many attractionslocation was great for all the parks and felt very safe as it's located in a quiet areaclose to the parks and shopping will definitely recommendfantastic stay the location was close & convenient for visiting all the disney parks + universal studiosthe location was great and easy to navigate to the parks or restaurants quickly
Superhost
2. Well-appointed home near Walt Disney World® Resort (from USD 171)
This beautiful home in Bellavida Resort is just a 10-minute drive from Walt Disney World® Resort. You will find all the facilities you need for a comfortable stay. The full kitchen is ideal to prepare meals if you don’t want to spend a buck dining out. Additionally, laundry essentials have been provided so you need not pack heavy.
The best part about this rental is that once you return after a long day of activities, you can plunge into the private pool or the whirlpool tub to rid your body of all the exhaustion. The pool can also be heated for an extra fee. The host also offers a barbecue set up for additional charges, so you can carry out a fun cookout.
In addition to the in-unit amenities, you can make use of the facilities at the resort’s clubhouse and keep yourselves thoroughly entertained. These include the community pool, whirlpool tub, gym and reading room, among others.
Top guest reviews
Amenities & Room:
there was definitely enough room for all of usCleanliness:
house was clean for the most partit was very clean and pool was perfect for kidsclean and huge lots of room for my familythank you for the cleanlinessRead more reviewsLocation:
great location very quiet neighborhoodthe location of the home is great to get to any destination in the area
3. Spacious rental in Country Creek Estates (from USD 190)
Here’s a beautiful rental located in Country Creek Estates. This home is equipped with all the amenities, including air hockey and a pool table for your indoor entertainment.
Alternatively, you can head to the pool deck and jump into the private pool to splash around a bit. A few pool toys and inflatables have also been made available to add to the enjoyment. Those who don’t want to step into the water can sunbathe as the deck receives sunshine all through the day. The transparent wall around the pool makes it possible to enjoy the serene lake views.
One of the bedrooms at the rental opens out into the pool deck. If you are intending to allocate this bedroom to your kids and are afraid that they may enter the pool unsupervised, do not fret as alarms are fitted into the deck door to detect any such activity.
Top guest reviews
Amenities & Room:
and the pool was delightfully heated to our amazeby far the best feature for us was the heated poolbeds were too firm for us but mattresses are pretty subjective so can't really complain about thatCleanliness:
everything was very clean and comfortablethe property was clean and had an excellent poolthe house was very clean pool is very nice close to walmart spacious safe arealoved the pool and it was very spaciousHost:
owners were very nice doing business with and even had toys available for the kidsRead more reviewsLocation:
the location was perfectclose to a lot fun attractionsgreat location and beautiful home for any family
4. Vacation home with hot tub (from USD 160)
You can consider checking into this neat rental located in a lovely neighbourhood in Cumbrian Lakes. Here, you can cool off in the private, screened pool shaded by a transparent wall affording views of the charming outdoors. Else, you can enjoy a warm, soothing soak in the private hot tub. After you’re done, you can enjoy quality family time thanks to the wide range of recreational options including board games, foosball, air hockey table, pool table and more.
Free, high-speed internet connection ensures that you remain connected to the world for work as well as leisure.
Top guest reviews
Amenities & Room:
very spacious and comfortable we have 7 people in our groupit was well stated this prop doesn’t provide things like washcloths paper towels toilet paper dish soap etcCleanliness:
the bathrooms were clean and comfortable to useupon arrival the home was clean everything was as described in the listingit was clean close to universal and disney and had everything that we neededHost:
very responsive management companythe host was a good communicator and made sure all my issues were addressedRead more reviewsLocation:
it was a good location and all amenities were close by
5. Carousel Villa (from USD 141)
Carousel Villa is a luxury accommodation located in a gated community at Kissimmee’s Cumbrian Lakes. The house is equipped with all the comforts of home. You can prepare a full meal in the kitchen and relish it in the dining area. Once you’re done, you can head to the private pool and refresh yourselves by swimming a few lengths. The pool can be heated for an additional charge, so you can consider dipping into it to relax your muscles as well.
After a fun swimming session, you can enjoy some indoor entertainment as there is a games room, where you will find a pool table, foosball table as well as air hockey.
Top guest reviews
Amenities & Room:
the kitchen was supplied very well and the amenities were all as stated in the vrbo websitethe heated pool was awesome would rent this house againgreat stay with a beautiful pool areaCleanliness:
clean good beds well stocked kitchenthis house was beautiful clean and a perfect find for our familyRead more reviewsLocation:
the location was close to everything and they enjoyed the gameroom
6. Comfortable accommodation with homey amenities (from USD 130)
Consider booking this rental if you’re looking for a home away from home in Kissimmee. Stocked with linens, towels, toiletries, kitchen appliances as well as laundry facilities, this house ensures a comfortable stay for its guests. Plus, the main bathroom features a soaking tub, where you can draw up a fun bubble bath for your little ones.
You can use the private pool to energize yourselves on a hot summer afternoon or pay extra to get it heated for full-blown relaxation. Some pool toys and inflatables have also been made available for your use.
Top guest reviews
Amenities & Room:
beautiful home equipped with more than enough amenities the private pool was so refreshing in the florida heatloved the privacy of the fenced in poolpool was nice for us to swim lots of floats for people to use of all agesCleanliness:
it looked like it hadn’t been cleaned in monthsthe house was nice the master bathroom wasn’t cleaned real good when we arrivedHost:
property was very nice property manager was super helpfulthe owners are amazing to talk to and respond very quicklywe were able to check in early after communicating with the owner so that was really appreciatedhosts very responsive to our request to stay next winterhouse was clean on arrival and the owner was super responsiveRead more reviewsLocation:
great location for shopping and restaurantsgreat location and close to all the attractionsthe location to disney and universal was perfectwe had plenty of privacy and the neighborhood is super quietthe neighborhood's very quiet and the houses are well kept and seem to be occupied which is nice
7. Spacious rental with high-speed internet (from USD 120)
At this spacious rental, you can plunge into the private pool and work on your swimming strokes. Else, you can pay additional charges to have it heated and spend hours soaking in it to rid your body of all the exhaustion. However, if you don’t want to pay extra, you can simply draw up a bath in the soaking tub in one of the bathrooms.
After a full day of fun, you can retire to the comfy bedrooms prepared to ensure restful sleep. One of them is specially prepared for children, so the young guests will be happy also.
Top guest reviews
Amenities & Room:
the pictures online showed there were four very nice looking lounge chairs around the poolCleanliness:
the house is spacious clean and comfortable and well equippedHost:
i contacted the owner and he said the manager will take care of itRead more reviewsLocation:
great location everything we need as a familygood location for any direction of travelwas a real nice house in a pretty nice location in kissimmeethe atmosphere is inviting and it is conveniently located to the shops and parks
8. Lakeside villa in peaceful locality (from USD 170)
This lakeside villa is located in Kissimmee’s Eagle Pointe community. At this rental, you can spend hours at the screened pool, either swimming or lounging next to it. There is a smaller, shallower section as well, so your little ones can splash around without your supervision. The soaking tub in the bathroom is another spot that you and your kids can enjoy.
To add to your indoor entertainment, there is a games room onsite. It is appointed with a ping-pong table, dartboard and several other facilities.
Top guest reviews
Amenities & Room:
it was perfect i'd rather have had the garage vs an non-air conditioned "game room" but overall very spaciousthe beds were very comfortable too which never happens in a hotelthe home itself was very comfortable and had all the necessary amenitiesCleanliness:
very clean jans cozyvery clean and welcominglovely house very clean the pool is just perfectthe house was very clean we would definitely stay here againneighborhood was very quiet pool was very nice and cleanHost:
the management was very responsive with two requests and friendlythe property manager was friendly and could be reached if neededRead more reviewsLocation:
the location and house will not disappointthe villa is in a great location with all needs taken care ofbeaches are not too far away and lots of great places to eat locally
9. Two-storey home in Lake Berkley Resort (from USD 148)
Book this great two-storey accommodation to spend relaxing time indoors. Else, you can head out to the private, screened pool to dip into its cool water. This can even be heated on prior notice at additional charges. Alternatively, you can lounge poolside and soak in the sunshine.
In addition to the private facilities, you can also use the resort’s shared conveniences. These include the communal pool, hot tub and basketball court among others. These are all excellent spots to mingle with the other guests staying at the resort, so you can head out to socialize a bit.
Note that quiet hours are to be observed between 10pm and 8am by guests staying in the rental unit.
Top guest reviews
Cleanliness:
we arrived at the house and everything was clean and organizedneeded a good all around deep clean and ac would not cool the house adequatelyHost:
the host phillip was phenomenal and super quick to respond and very friendlyphillip was very accommodating for our large party last minute extremely responsivethe pool was amazing and the owner was extremely responsivea good sized house for our big group and the host was extremely responsivegreat house and a lot of fun owner is great and super cooperativeRead more reviewsLocation:
location was greatgreat location and great valuegreat location and excellent value for the pricegreat location the beds are very comfortablethis place is beautiful and near all kinds of family activities
10. New home with themed rooms (from USD 380)
Book this brand-new, charming vacation retreat and spend a memorable time with your loved ones. At this multi-storey home, you can spend hours unwinding in the living room, else you can head to the equipped games room and challenge your buddies to a bit of competition. You will find a PlayStation, pool table and several other games here.
Alternatively, you can dive in the private pool and swim a few lengths. Right by the pool, you will also find a private hot tub, which is ideal for a calming soak. If you are booking this place for five nights or more, you can also opt to have the pool heated for an additional fee.
Note that quiet hours are to be observed after 10pm.
Top guest reviews
Amenities & Room:
the game room made it so easy to keep all the kids (all ages) entertainedwe loved the hot tub pool and game roomthe house was absolutely immaculate upon arrival with thoughtful ambient lighting and dining table setthe house has many rooms and the game room is amazingCleanliness:
our host was the best at communication and the property was very cleanbathrooms in each room everything was so neat and cleanHost:
the host were amazing they responded immediately anytime we reached outRead more reviewsLocation:
walmart super store is 2-3 min up the streetgood location lots of places to eat as well as being close to many attractions in orlandothe location was good not far from the parksthis is a fantastic place to stay
Enjoy a relaxing vacation in Kissimmee
Kissimmee is a classic family-friendly destination. It is home to charming attractions and comfortable lodging facilities that make several travellers see it as a great alternative to staying in Orlando. Choose from one of the excellent accommodations listed in this article and you should be good to go for an exciting and relaxing trip to Kissimmee!
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