Kissimmee, Florida is perfect for family vacations at theme parks, a getaway with friends, or just a romantic outing with your partner. This family-friendly town is within a few minutes’ drives from Walt Disney World Resort. When you have had your fill of the Disney magic, there’s also Universal Orlando Resort and SeaWorld Orlando nearby. Apart from theme parks, there’s also a lot on offer for nature and adventure lovers. You can zip through treetops, glide across the headwaters of the Everglades, get a close view of alligators in the Airboat and Gator Park, or soar over the lush landscape in a hot air balloon. If shopping and lounging in cafes is more your style, there are several malls, including The Florida Mall and The Mall at Millenia, with premium designer boutiques. You can feast at the top restaurants in town as well. Do these attractions make you want to visit Kissimmee this year? Here is a list of Kissimmee vacation rentals with private pool.
1. Gorgeous four-bedroom townhome in Storey Lake Resort (from USD 173)
A brand new luxury townhouse close to Disney World, Universal Studios, Sea World, numerous outlet malls, Orlando attractions, Disney Springs, restaurants, and dining. There’s enough space for eight guests with four bedrooms, three baths, a large living room, and a state of the art kitchen. What’s special about this house is the beautiful decor with cozy furnishings. There’s a private pool with lanai screens where you can swim and relax after a day of sightseeing. Children can also head to the clubhouse with a large pool, a water slide, and a long lazy river to play and splash about. Families will surely enjoy this Airbnb in Kissimmee, Florida with a pool.
Minutes To Disney, Private Pool, Amenities,PEQ3141Kissimmee, Florida, United StatesTop guest reviews
Amenities & Room:
the washer/dryer refrigerator and small appliances were nice and the kitchen well stocked with suppliesthe villa is huge with a beautiful view from pool area looking onto a lakegreat for families with a fully equipped kitchen and three full bathroomsthe beds were comfortable and the kitchen was spaceythe place was tip-top and very comfortableCleanliness:
very clean and spaciousclean and beautifulvery clean and quiet neighborhoodbeautiful house clean and comfortableit was very clean and had everything we neededHost:
thank you for being great hostsclint was ultra-responsive and ready to help with any questions or concernsexcellent communications from the hostRead more reviewsLocation:
great location and really spaciousthis place was great location is greatfantastic place and great locationgreat location close to parks and groceriesit’s just a short nice walk to the clubhouse
2. Beautiful seven-bedroom lake house (from USD 221)
Live in a sparkling clean, beautiful lakefront home that can accommodate a gathering as large as 16 people. It is conveniently located near theme parks, malls, and restaurants. There are seven bedrooms, a spacious living room, a kitchen, a games room, as well as access to the resort’s community pool, a community hot tub, a gym, sports facilities, barbeque, and a picnic area. All the beds have comfy memory foam mattresses. There’s a beautiful lake view and free WiFi. At this Airbnb in Kissimmee, Florida with a private pool, you also have a spa with heating.
The Lake House! 7Br 4.5ba with private pool!Kissimmee, Florida, United StatesTop guest reviews
Amenities & Room:
plenty of room a wonderful pool and deck with a view of a beautiful lakethe sunrise from the pool looking out over the lake is beautifulkids loved the pool and the area has amazing amenities such as playground and tons of ducksloved all the different rooms - plenty of space for everyoneloved the many bathroom and game roomCleanliness:
very clean lots of spacebathrooms were clean but need a much deeper clean in the shower windowswe found this home very clean and well furnishedthe bedding was fresh & cleanvery beautiful clean and modern house to stay with friends and familyHost:
great hosts and a wonderful propertythe hosts were quick to respond and very pleasantthe owners were very responsive anytime i contacted them they answered right awayamazing property and wonderful responsive hostsusually host write you the day of just to make sure you have key pointsRead more reviewsLocation:
great location about 25 minutes drive to disney world universal studios and the airportthe location was perfect for our needsthe location is great and there is a great path to walk around the lakewould definitely recommend everything is fairly close and the house is greatthe house was beautiful with the perfect location
3. Gorgeous villa for a large group (from USD 656)
This is a great villa in Kissimmee for a big family reunion or a gathering of friends. The highlight of the property is a unique Batman-themed game room that guests of all ages will love. Plus, there is a private pool, a spa, a shaded patio with an alfresco dining set-up, sun loungers, and more. Inside, the villa has a luxe and trendy decor in the living, dining and kitchen areas. Nine gorgeous bedrooms and five contemporary bathrooms are also available in the villa. Disney and Universal theme parks are just a few minutes’ drive away.
LARGE VILLA* Private Pool *GAME ROOM* TheaterKissimmee, Florida, United StatesTop guest reviews
Amenities & Room:
there were marks up the walls the tiles in the bathroom weren’t completely cleanRead more reviewsHost:
amazing home and very kid friendlythe host was awesome and my family will definitely be returning back
4. Well-appointed home with easy access to theme parks (from USD 330)
Suitable for large families or groups of friends on a vacation in Florida, this eight-bedroom, six-bathroom home can accommodate up to 18 guests. It has a very luxurious interior consisting of a well-appointed living area, a large dining area, a full kitchen, a game room, lavish bedrooms and elegant bathrooms. A gorgeous private pool, a spa, and an outdoor deck with seating are available too. Guests even have access to the resort’s facilities like a massive swimming pool, a clubhouse, and a kids’ play area. Many of Orlando’s famous theme parks are a short drive away from this property.
Luxury Disney Dreamers Wonderland @Windsor Westside Resort,Private Pool,GameRoomTop guest reviews
Amenities & Room:
well appointed; comfortable amenitiesthe home is great air conditioned game room pool an amazing supply of pool toysCleanliness:
the house was very clean and spaciousthe pool at the house was impeccably clean and warmit’s a beautiful home and very cleanwonderful property well kept and cleanbeds were comfy and bathrooms cleanRead more reviewsLocation:
great location for large group to enjoy all attractions in the areagreat location close to attractions yet had a feel of being away from the crowdslarge rooms and we would definitely come back you are 20-25 min from parks but drive is easy
5. Stylish townhome with amazing amenities (from USD 162)
For a family holiday in Florida, book this amazing townhome in Bela Vida Resort that is just minutes away from Disney theme parks. Well-appointed and stylish, this home has a stunning interior done up in white, gray, beige and brown. An open-plan living and dining area is located next to a contemporary kitchen. Four luxurious bedrooms, three elegant bathrooms, and a game room complete the interior of the house with amazing amenities. You will also have access to a screened private pool, spa and patio area.
4-bedroom house w/ private pool - lovely locationKissimmee, Florida, United StatesTop guest reviews
Amenities & Room:
great interior and fun for the kids with an air hockey and billiard tablenice to have a comfortable place closed off from the mayhem of the tourist areasthe game room in the garage was perfect for rainy florida daysCleanliness:
house was clean and goodthe dishwasher is not working well so we had to clean the dishes by handgreat house really clean really quite neighborhood had a great timebe sure to not forget to bring cleaning stuff alsothe house looks good and is clean but didn't make for a good relaxing vacation spotHost:
host is excellent communication was on point with any concernsRead more reviewsLocation:
amazing house amazing location just all around amazingwe had a wonderful stay at this locationthe home is also located at a very great locationwill definitely be booking this place for future tripshome highly recommended very well located everything perfect
6. Luxurious lakefront family villa (from USD 140)
This beautiful five-bedroom villa, situated beside a lake with a fountain, comes with all the amenities needed for a luxurious vacation. It can comfortably house 11 people. There’s a fully equipped kitchen, spacious living and dining area, a charcoal grill, free WiFi, digital entertainment, linen, and laundry facilities. The star attraction of the house is the huge, clean pool where you can relax and swim in privacy.
Exquisite Destination. Disney Vacation Homes. Central to All Major AttractionTop guest reviews
Amenities & Room:
some i gave up on but it was still awesome having tvs in every room and outsidegreat rooms entertainment w tvs all over the house including out on the pool sidewe were able to enjoy the pool and pool table during our off timethe pool was nice and warm for the kids loved this house thanks xedxb8x8aCleanliness:
the property was super clean the linen and towels smell so goodthe house was very cleanvery relaxing the place was very clean which was important to usthis house is well stocked and cleanme and my family felt like we were home the pool was clean the kids enjoy itHost:
very responsive management company to any questions we hadrenting was easy correspondace with the owner was a plus and we certainly felt like we were welcomeRead more reviewsLocation:
we love this place location and neighborhoodgreat location beautiful home and gorgeous decor we felt at home and comfortable in this property
7. Spacious home away from home (from USD 110)
If you’re looking for Kissimmee vacation home rentals with a private pool and a convenient location, then this property might interest you. This large three-bedroom home in Kissimmee is just an eight minutes’ drive from the Walt Disney World Resort area. The air-conditioned house offers all the necessary amenities. There are comfortable hardwood-floor living, dining, and kitchen spaces. All the bedrooms have flat-screen televisions and huge walk-in closets where you can store all the new clothes you buy at the Florida malls. After a day out, you can relax in the fully fenced garden area with a solar-heated pool and spa. There are lounge chairs by the glistening pool where you can stretch out and get a glorious tan.
SUPERB POOL HOME CLOSE TO DISNEYTop guest reviews
Amenities & Room:
Everything you could possibly need provided The pool was larger than we expected and lovely and warmThe house is very comfortable with a fantastic pool kitchen equipped with everything you may need during your stay luxurious beds wifi and 1000s of TV channelsLovely villa well furnished fantastic pool plenty of poolside furniture everything as I expected it to be Will be backThe villa is so comfortable you instantly feel at homeVery relaxing time with many hours spent by the pool couldn't have asked for anything betterCleanliness:
It's lovely clean and spacious with a great poolwe were so pleasantly surprised at how spacious and inviting the home lookedHost:
Warm and welcoming felt at home straight awayWe had a small issue with the stove during our stay and he sent an electrician out that same day to look into itPool is cleaned and maintained by a professional company once a week Mike is an awesome person to work with with any questions or concerns that you might haveit was replaced with a brand new ceramic top stove within a week The Hunter family who take care of the home are simply the bestThis beautiful home was very comfortable and enjoyable for our familyRead more reviewsLocation:
location is brill queit area but near to amenitiesGreat location Quiet neighbourhood and easy access to all amenities and attractions Maintained and spaciousThird visit to this villa just booked the 4th visit great location to the Disney parksNo problems Loved it all weekthat is an indication of the popularity of this property
8. Modest home with a screened-in pool (from USD 122)
One of the most affordable places a family or group of up to eight people can rent is this Indian Point home with four bedrooms. The furniture and decor are modest while still exuding luxury and comfort. The living area is equipped with entertainment facilities like the television and DVD player, while the kitchen is fully functional. Free access to Wi-Fi is available at the property as well. The Disney theme park is a short drive from this modest home.
Private Secluded Pool - Less than 8 miles to DisneyTop guest reviews
Amenities & Room:
screen in pool deck was nice kept bugs mosquitoes and flies awayCleanliness:
it was great and clean will stay there againcleaning company could use some coaching but house itself spacious and comfortableleft it all there for the next person & cleaned it better than when we arrivedwe had to clean the place & we found stuff from previous guestsit was a relaxing time but would have enjoyed not buying so many cleaning supplies & bug stuffHost:
owners were super responsive to my questions/issueshad a small issue and the owners contacted maintenance getting it taken care of the next morningproperty was amazing will stay again owners are absolutely the bestRead more reviewsLocation:
the house was in a great location close to everythinggreat time for a quiet break long neededwe were happy to have booked this locationpool was great break after long day at the parksclose to parks great master suite awesome house for kids and nice pool and patio area
9. Single-story Lake Berkley home (from USD 155)
This budget-friendly vacation rental in Kissimmee is located in a private, gated community. Staying at the property is ideal for families with young ones since there are plenty of entertainment amenities like the game room with a billiards table, a dartboard, a play area, and many more. The 24-hour Walmart is 2 minutes from the property, and guests who wish to make use of the full kitchen may do so. Outside, there is a screened-in and heated swimming pool with a shaded seating area.
Single Storey 5 Bed 3 Bath Villa with Pool, HD-TV , private beach + WiFiKissimmee , FL, USTop guest reviews
Amenities & Room:
the pool was perfect - nicely heated for the little oneseasy wifi access comfortable rooms and eat instruction manual that answered all other questionsmy families stay was so much more comfortable and enjoyable because of itthis property was awesome we were 5 adults and 5 kids it was spaciuos with enough room for everyoneCleanliness:
everything was clean and very nicethe property was clean and comfortableit had plenty of space and the house was clean and well maintainedupon arrival at this villa the overall appearance was neat and cleanthe home was clean and well maintained and we did not expereience a single issue during our stayHost:
betina and annette were very helpful in the many questions i hadi had a chance to meet the owners and they ere very friendlythe owner was 100% correct and very gentlefriendly gate peopleeven the guard at the gate was very helpful in giving directions to the many different attractionsRead more reviewsLocation:
the location was great - so close to shopping and eatingvery good location close to restaurants and dinner showsall very accessible and easy to get to from the locationperfect for big family great location would recommend to everyone vacationing with 6 or more peoplealso we visited several attractions in the area all very close to the villa -- easy
10. Cozy pet-friendly waterfront home (from USD 109)
This clean and comfortable house can accommodate up to seven guests. You can drive to Disney World within 15 minutes, Seaworld within 20 minutes, and Legoland within 40 minutes. There are all the necessary amenities to make your stay comfortable: two lounge areas, a large fully-equipped kitchen with a dining area, outdoor dining on the lanai, an outdoor grill, games room, and free Wifi. What makes it one of the most beautiful Kissimmee home rentals with a private pool is the south-facing, private, screened pool and Jacuzzi overlooking a scenic pond.
Pet Friendly 3 Bedroom/2 Bath Home,Games Room, Private Pool & Spa.Top guest reviews
Amenities & Room:
There was plenty of spaceEach of the 2 baths only had one partial roll of toilet paper that ran out quickly No paper towels in kitchenThe weather was kinda touch n goWe enjoyed playing on the pool table inside the garage / recreation room in the eveningsThe kitchen and living spaces are enormous and more than enough for most familiesCleanliness:
It was clean and nicely locatedThe house was clean with anything you can need Pool clean and comfortable overall great placehowever the beds were both very comfortableWell designed clean house in a quiet neighborhood with plenty of space in most roomsand I mean tiny) bar of soap in both bathsHost:
Marion was also great about responding quickly to any questionsWe all four loved the pool especially our girlsThere is an elongated wetland / pond about 100' away with an abundance of tweety birds and waterfowl all aroundMy kids really loved the good sized poolit was a wonderful experience and the owner was always available if I need any questions answered Thank you againRead more reviewsLocation:
Regardless of the supplies issueThe neighborhood was quiet and close to Disney WorldThe location was easy to find and not too far from restaurants and fun in Orlando FloridaNeighbours were wonderful Not far from WalmartThis house is centrally located in a quiet neighbourhood
11. Luxurious home in a gated community (from USD 180)
Professionally decorated and appointed with luxurious amenities, this beautiful home is located in the gated community of Veranda Palms. Ideal for large groups of up to 16 people, it has six luxe bedrooms, four and a half bathrooms, three gorgeous living rooms, a game room, two dining rooms, a modern kitchen, and more. Outside, you can relax in your private pool or enjoy a relaxing soak in the spa. Prepare barbecue meals for everyone that you can enjoy at the alfresco dining area. All famous theme parks are a short drive away from this house.
6BR/4.5B, Private Pool/SPA, 10mi Disney. Amazing!Kissimmee, Florida, United StatesTop guest reviews
Amenities & Room:
the amenities like the pool game room and the grill are what most impressed methe game room kept my kids entertained playing pool and air hockeythere was a very fierce storm with huge hailstones which dashed the screen around the poolthe kids loved the pool and the jacuzzi and the large game roomlots of space and game room and pool loved so muchCleanliness:
the house is beautiful clean and modernthe house was great clean and spaciousthe rooms were very clean and comfortablevery clean spacious and up to datepool is fun and the house was very cleanHost:
also the host was greathosts were greatand the host douglas was very helpfulawesome property with amazing hostsdouglas the host was great great response time and very considerate and helpfulRead more reviewsLocation:
location was great and quiet neighborhood close to everythingthe location is wonderfulgreat location and comfortable houselocation is great as wellalso an ideal location close to disney
12. Disney-themed townhome in a resort (from USD 179)
Your kids will absolutely love staying at this Disney-themed townhome in Bella Vida Resort. This family and pet-friendly home offers luxurious living with a touch of Disney magic in its decor. Relax in the open-plan living, dining and kitchen area that looks out to the private pool. Four themed bedrooms and three spacious bathrooms are available for the use of up to 10 guests. The pool area has a barbecue grill and sun loungers too. Disney parks are at a 15-minute driving distance from this townhome.
Near Disney 4BR Family Resort Home - Private Pool!Top guest reviews
Read more reviewsCleanliness:
upon check in the house was clean and smelled amazing
13. Chic home with resort clubhouse access (from USD 580)
When visiting Kissimmee, consider booking this chic and stylish home in Sonoma Resort that provides access to a range of resort amenities, including a clubhouse, a gym, and a gorgeous communal pool that overlooks a lake. The house has a screened private pool, a spa, a barbecue grill, and ample sun loungers to enjoy the Floridan outdoors. The interior of the house has a modern, chic and minimalist decor in the living room, open-plan kitchen and dining area, luxe bedrooms, stylish family room, and sleek bathrooms. All the attractions of the area, including theme parks, nature parks, restaurants, and more are at a short driving distance from this home.
14 Bedrooms Luxury Home at Sonoma Resort KissimmeeKissimmee, FL, US
14. Deluxe pool home
A beautiful four-bedroom house, it comes with air conditioning, internet, laundry facilities, and a well-equipped kitchen. The master bedroom opens onto a lovely pool deck. Spend your mornings sipping coffee as you watch big Florida birds fly over the lake. Have fun in the well-maintained swimming pool with seating around it. Sunbathe on a lounge chair or have your meals at the table by the pool. You can also play foosball and ping pong in the garage or have a relaxing soak in the garden tub.
Lakefront Pool Home - Minutes to Disney FREE POOL HEAT FROM 4/ 5 TO 4/18/21Top guest reviews
Amenities & Room:
This property looked exactly like the picturesthe kids enjoyed the poolIt was great to have access to a grill and not have to had to pay extra to use it loved having access to the pool from the master bedroomIt was clean inside and out with a well equipped kitchen plenty of outside space some of which is covered which is handy when it rains It has a lovely lake view with an abundance of wildlifeThe only thing is I wish they would have provided a few more trash bagsCleanliness:
everything was clean and everything we neededThe villa was clean spacious and had everything we neededThe place was clean and well equippedand we were amazed with your houseHost:
the key lock box was not secure & the pool net was torn)The pool was a big hit with my girlsWe have already booked for next yearOverall the property was nice and exactly as advertisedBeautiful clean updated home Beds were super comfortableRead more reviewsLocation:
Very lovely house in a great locationI liked the quiet neighborhoodThe house Is very close to Disney World and a good base for exploring the area (including the Kennedy Space Centre which is well worth a visit)Location was ideal for visiting parks or shoppingThe neighborhood was quiet and peaceful
15. Unforgettable vacation home near Disney World
A modern and stylish house within 4.8 miles (7.7 km) of Disney World, 11.5 miles (18.5 km) of Universal, 7.8 miles (12.5 km) from Sea World and within an easy drive from other major attractions. You have a kitchen with everything you need to cook your meals, Wifi, cable TV, laundry facilities, a laptop-friendly workspace, and access to the clubhouse of the resort. And, you get to enjoy two luxurious resort pools one of which comes with a lazy river. Stay here for a comfortable and fun holiday.
Luxury near Disney - Pool HomeKissimmee, Florida, United StatesTop guest reviews
Amenities & Room:
wifi in the house is greatwe had comfortable beds and great amenitiespools were great and everyone had a great timethe pool was terrific and privatethe kids loved both the private pool and community pool with lazy river and water slidesCleanliness:
everything was clean and felt extremely sanitarygreat place very clean and spaciousthe house is beautiful clean and very spaciousit’s was super clean and homeyvery nice and clean place modern and stylishHost:
adriana was a great hostshe was very responsive and accommodatingadriana is a great hostadriana’s is an amazing hostvery good house and great hostRead more reviewsLocation:
the location was excellent and very convenientalso loved the locationgreat location beautiful house in gated communitygreat community for family vacationing shopping center really close bythe location is excellent to all the florida attractions
16. Centrally located six-bedroom holiday villa
This holiday home, located in Aviana Resort, is within a 20 minutes’ drive from Disney World and close to all other major tourist spots in Orlando. The spacious six-bedroom home comes with all the amenities needed for a comfortable stay. You get to enjoy Aviana Resort facilities as well: a stylish clubhouse, a picnic area, a sand volleyball court, beach access, and a children’s playground. There is also a huge resort-style pool with screens for privacy. You can avail pool heat at an additional cost.
Beautiful 6 Bed Gated Pool Home At Aviana Resort
17. Comfortable three-bedroom house with a pool
Stay in this luxurious three-bedroom villa with a large family room that opens into a patio with a pool, a lounge room, dining room, and a well-equipped kitchen with a breakfast bar. Relax in the en-suite master bedroom that comes with a jacuzzi. The beautiful house pool, screened for privacy and equipped with loungers, a table, and chairs, is perfect for some family fun. There are ample parking spaces and a sprawling lawn that opens into a wooded area.
Luxury 3 bedroom villa with private pool2701 shortleaf court
18. Great vacation home near Disney World
You are going to love this four-bedroom home on Indian Ridge within a few minutes drive from Disney World. As the house is professionally managed, you’ll have 24 hours guest service. There are all the necessities here, like a fully equipped kitchen, a game room, laundry facilities, parking, air conditioning, and much more. In addition, the house has a beautiful private pool where you can relax and have fun.
GAMEROOM, BBQ GRILL, FREE WIFI, ONLY MINUTES FROM DISNEY!!1539 Indian Oaks Trail
19. Townhome with access to resort amenities
Stay at a lovely townhome in Kissimmee that can comfortably sleep 10 guests in its 4 bedrooms. The house has a well-appointed living room, a modern kitchen, a lovely dining area, and spacious bedrooms and bathrooms. A private pool with a patio and seating are also available for guest use. Resort amenities like a clubhouse, an arcade, a market shop, a massive pool, a fitness center, and more are also accessible to guests staying at this property. Walt Disney Resort is just 5.5 mi (8.9 mi) away.
Full-service Tiki Bar / Water Slide / Fitness Center / Movie Theater / Near Disney /Free Resort FeesTop guest reviews
Amenities & Room:
kids loved the heated poolthe kitchen area is great size for familiesboth couples had rooms with king beds and the trundle beds worked perfect for the kidsCleanliness:
full kitchen everything clean and newHost:
the staff and everyone were really helpful and kindRead more reviewsLocation:
we loved our stay the house was located close to everything we wanted to dowe loved how close it was to disney parks
Fall in love with Kissimmee
Kissimmee is the place where all your holiday dreams can come true. Once you’ve been here, you’ll keep returning for the excitement, joy, Disney magic, and natural beauty. And whether you’re looking for lakefront homes or beach house rentals with a private pool, plenty of amazing accommodation options are available in Kissimmee.
Frequently asked questions about Kissimmee vacation rentals with a private pool
1. Which Kissimee vacation rentals with a private pool have nice views?
This beautiful seven-bedroom lake house, this luxurious home in a gated community, and this chic home with resort clubhouse access are the vacation home rentals with a private pool in Kissimmee that have nice views.
2. Which Kissimee vacation rentals with a private pool are good for families?
Make your family trip to Kissimmee more memorable by staying at any of these vacation rentals with a private pool that are most suitable for you: a modest home with a screened-in pool, a single-story Lake Berkley home, and a luxurious lakefront family villa.
3. Which Kissimmee vacation rentals with a private pool have a gym?
This chic home with resort clubhouse access and this beautiful seven-bedroom lake house are the vacation home rentals in Kissimmee that offer gym access to guests.
Get Trip101 in your inbox
Unsubscribe in one click. See our privacy policy for more information on how we use your data
Create an account to bookmark our articles, like local expert tips, receive great stories in your inbox, and follow writers and topics that you love.
Log in with Facebook Log in with Twitter Log in with Google ×