
Villa holiday rentals in Kissimmee
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Top-rated villa rentals in Kissimmee
Guests agree: these villas are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for villa rentals in Kissimmee
Private villa rentals

Villa
4.7 out of 5 average rating, 89 reviewsDisney area 4-bedrooms spacious villa for rent
House was as pictured and was very comfortable inside!

Villa
4.73 out of 5 average rating, 15 reviewsBeautiful Disney Disney Resort Villa w/ Pool
We had such a lovely stay! The place was just as pictured. Plenty of space for the 9 of us to lounge around the house and hangout by the pool. We will definitely be back!

Villa
4.95 out of 5 average rating, 40 reviewsGraystone Villa, 3 bedrooms with private pool
My family and I enjoyed this location. It was the perfect size for us and most of all we enjoyed the private pool. The only thing is we paid for the pool to be heated and it really didn’t feel like it was actually heated, so it felt like a waste of money for that added feature. Other than that it was great. Nicola was always available when needed and kind to us. We definitely would stay here again.

Villa
4.83 out of 5 average rating, 69 reviewsLuxury 9Beds Villas With Pool Spa In Solara
This was our second time staying at Chuck’s place. The resort amenities are great and our family utilized the splash pad, pool, gym, basketball courts and restaurant. The house is great and accommodates our family of 14 perfectly. We had a great stay!

Villa
4.73 out of 5 average rating, 56 reviewsPrivate Villa with Pool near Disney
It was a great place to stay. We would not hesitate to stay here again if we are in the area.

Villa
4.8 out of 5 average rating, 81 reviewsSeasons Retreat, 5 Bed, 4 Bath, Private Pool Villa
George was an exceptional and amiable host. He demonstrated exceptional responsiveness and provided invaluable assistance in addressing all my inquiries. The heated pool was particularly noteworthy, enabling us to fully appreciate the cold temperatures despite the low season. The arcade room offered an enjoyable alternative for those who prefer indoor activities and limited outdoor excursions. The accommodations were spacious and well-appointed, featuring multiple rooms and bathrooms to accommodate all guests. Furthermore, the surrounding neighborhood was characterized by tranquility and ample parking. I highly recommend George’s place and would eagerly consider booking another stay.

Villa
4.76 out of 5 average rating, 149 reviewsJas Vacation Home 314
Beautiful home ! Stunning neighborhood! Everything was just as pictured. Communication with the owner was easy and he was very quick to respond.

Villa
5 out of 5 average rating, 6 reviewsNew 7 bed villa with game room. Free waterpark.
Enjoyed my stay definitely worth the price we will be next year
Luxury villa rentals

Villa
4.84 out of 5 average rating, 50 reviewsPrestige 5: Lux Windsor West, S Fc Pool, Lake View
We’ve just returned from a large family holiday! With family flying in from Boston and Las Vegas, Orlando was a central location for us to kick back & enjoy each other’s company. Plenty of space for our 13 person group! The pool and hot tub were perfect, large kitchen where we cooked big meals & fun game space on the 2nd floor! We enjoyed a day at the club house & pool - a quick walk from the home we stayed in. Loved having a lake behind us, making it feel peaceful and private. Communication before, during & after was easy and prompt.

Villa
4.94 out of 5 average rating, 87 reviewsBlue Paradise-15 Bdrms, Sleeps 32-Theater, GameRm
The house was absolutely wonderful! Easy to find and conveniently located near shopping, with no issues getting Instacart deliveries. Everyone kept commenting on how fun the house was - extremely spacious and elegantly designed inside. Everything was well-maintained and in perfect working order. The pool was lovely, and all our guests had a fantastic stay. We would definitely stay here again!

Villa
4.98 out of 5 average rating, 97 reviewsClose to Parks, 8Bd, Karaoke, Pool, Spa, Theater
Stephanies house was exactly as described. Beautiful house overlooking the lake and even got to see the resident alligator swim by! Pool was cool and spa was hot! Definitely would recommend staying! We will book again for sure😊

Villa
4.58 out of 5 average rating, 12 reviewsDisneyMansion 14 Rooms 11BR/5BA with Golf Package
This booking was a last minute booking as another host canceled our stay 30 minute before checking only because I called to get the codes to the door. Ann and Lars to the rescue they accommodated my whole family in their spacious home and the rest was history. The place is clean and has plenty of beds to rest about 24 to be exact so if you traveling with a large party and need accommodations don’t hesitate to send them a message, they respond back pretty quick and are willing to work with you. The place was cleaned and the TVs are a plus when you back home from your adventures and want to catch up on your shows (Netflix) included. Again don’t hesitate to send them a message and see if it’s available. Thanks Ann and Lars for the accommodations. Great job making it feel homey.

Villa
5 out of 5 average rating, 79 reviewsThe Golden Bear Villa | Private Pool & Theater
Convenient location. Great pool and spa. Rooms are well appointed for 6 adults. With two extra rooms for kids! Loved the theatre room! Dan is super responsive to our questions.

Villa
5 out of 5 average rating, 3 reviewsBeautiful Villa Champions Gate 6Beds/5Bath/Pool/Ja
Beautiful home, matches the pictures, and everything works great! Loved the up-stairs home theater and the private pool and spa. Lovely resort and amenities! The host is very quickly-responsive and accommodating which made the entire experience even better! Highly recommend and would definitely stay here again!

Villa
5 out of 5 average rating, 20 reviewsWindsor Island Villa
The house was just the way it looked in the pictures! We totally enjoyed the arcade room! Lots of friendly competition happened in there. My granddaughter loved the themed bedrooms. Although we had cooler weather, having the pool heated allowed us to get in a little swimming. We walked up to the clubhouse and had some good cocktails and snacks. Location was perfect for us to visit the Magic Kingdom, Epcot and Disney Springs. I would highly recommend this house, especially if you have a few kids with you. They won’t want to leave!

Villa
5 out of 5 average rating, 8 reviews9BR/6BA Pool Resort Villa 5 mile to Disney #4049J
Love the house ..very spacious. Beds were wobbly but we spoke with Maintenance and they were responsive. Great area , short walk to the community. I will be booking again in the future.
Villa rentals with a pool

Villa
4.96 out of 5 average rating, 170 reviews4 bed villa w/private pool near Disney, sleeps 6+
We had a great stay. The house was wonderful and close to activities. Hosts were very responsive and friendly. A++ stay. Thank you!

Villa
4.83 out of 5 average rating, 77 reviews5bedroom,pool,18min to Disney, Kissimmee davenport
Miguel's home was more then we expected. He communicates very well , and was also very helpful

Villa
4.88 out of 5 average rating, 8 reviewsSpacious Multi Family Villa- 6Br Sunny Pool Deck!
We enjoyed our stay! The host was accommodating, responsive, and friendly. Clean, spacious, and worth the price. Look forward booking with them again.

Villa
4.74 out of 5 average rating, 76 reviewsNr Disney pool/cinema room/outdoor kitchen
This was a beautiful villa in an ideal location, not far from Disney parks. Very spacious, clean and great layout. Particularly enjoyed the cinema room in the villa, we have a lovely family evening watching films. Lots of personal touches and Paula was an absolute joy to book with, very helpful and quick to respond...would definitely book here again, thanks for the lovely stay.

Villa
5 out of 5 average rating, 24 reviewsLuxury Villa Pool/Spa 2 Masters, Highlands Reserve
10/10 would recommend this vacation home! Beautiful, spacious home with an awesome outdoor living area. We thoroughly enjoyed the pool and spa as well as the outdoor dining/fire table area that comfortably seated our entire family. The kids really liked the game room. The beds and pillows throughout the home were very comfortable. Dawn was a great host and she has fully stocked the house with all the supplies you could ever need. Plenty of extra towels, blankets, pillows, kitchen items, etc. She even keeps it stocked with a few convenient snacks as well as essentials like spices, coffee, tea, dishwasher tabs, dish liquid, cleaning supplies, etc. There are even little baskets in the bathrooms filled with things you may have forgotten such as toothbrushes, toothpaste, Q-tips, etc. Since we were there around Christmas time, there was a cute little Christmas tree, stockings and a couple of other decorations around the house. She really has thought of everything!

Villa
4.86 out of 5 average rating, 36 reviewsSouth facing Modern villa in quiet gated estate
Our family and I had a very pleasant stay at Melanie's home. Everything in the property was exactly as shown on the listing, and the space was found in pristine condition. The neighborhood lent itself for very peaceful walks in the morning, and we liked that the pool was secluded behind a few trees. Our vacation could not have been the same without the hospitality we received from our stay here!

Villa
4.78 out of 5 average rating, 83 reviews4-bed villa w/ beautiful pool 15 mins from Disney!
It felt right at home from the moment we arrived to the minute we left. Every thing was clean, comfortable and overall a wonderful experience. We would definitely stay there again. Thank you for your hospitality in letting our family stay in your beautiful home. Brittni

Villa
5 out of 5 average rating, 29 reviewsSharedale Lakeside Villa
The house was absolutely perfect for our family! Lilliana was very accommodating as we needed to check in rather immediately. Clean, comfortable, exactly what we were looking for! Will definitely reach out for our next vacation.
Quick stats about villa rentals in Kissimmee
Total rentals
790 properties
Nightly prices starting at
£24 before taxes and fees
Total number of reviews
18K reviews
Family-friendly rentals
770 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
730 properties have a pool
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