Villa holiday rentals in Kissimmee

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Popular amenities for villa rentals in Kissimmee

Private villa rentals

Superhost

Villa

4.7 out of 5 average rating, 89 reviews

Disney area 4-bedrooms spacious villa for rent

AndrewRating, 5 stars2 months ago
House was as pictured and was very comfortable inside!
Superhost

Villa

4.73 out of 5 average rating, 15 reviews

Beautiful Disney Disney Resort Villa w/ Pool

JessicaRating, 5 stars20 months ago
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!
Guest favourite

Villa

4.95 out of 5 average rating, 40 reviews

Graystone Villa, 3 bedrooms with private pool

ReneishaRating, 5 stars6 months ago
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.
Superhost

Villa

4.83 out of 5 average rating, 69 reviews

Luxury 9Beds Villas With Pool Spa In Solara

SusanRating, 5 stars2 months ago
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!
Guest favourite

Villa

4.73 out of 5 average rating, 56 reviews

Private Villa with Pool near Disney

PhilipRating, 5 stars1 month ago
It was a great place to stay. We would not hesitate to stay here again if we are in the area.
Guest favourite

Villa

4.8 out of 5 average rating, 81 reviews

Seasons Retreat, 5 Bed, 4 Bath, Private Pool Villa

AdrianRating, 5 stars2 months ago
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.
Superhost

Villa

4.76 out of 5 average rating, 149 reviews

Jas Vacation Home 314

DashelleRating, 5 stars2 months ago
Beautiful home ! Stunning neighborhood! Everything was just as pictured. Communication with the owner was easy and he was very quick to respond.
Guest favourite

Villa

5 out of 5 average rating, 6 reviews

New 7 bed villa with game room. Free waterpark.

JasmineRating, 5 stars1 month ago
Enjoyed my stay definitely worth the price we will be next year

Luxury villa rentals

Superhost

Villa

4.84 out of 5 average rating, 50 reviews

Prestige 5: Lux Windsor West, S Fc Pool, Lake View

CarrickRating, 5 stars18 months ago
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.
Guest favourite

Villa

4.94 out of 5 average rating, 87 reviews

Blue Paradise-15 Bdrms, Sleeps 32-Theater, GameRm

NicoleRating, 5 stars2 weeks ago
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!
Guest favourite

Villa

4.98 out of 5 average rating, 97 reviews

Close to Parks, 8Bd, Karaoke, Pool, Spa, Theater

StacyRating, 5 stars6 days ago
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😊
Superhost

Villa

4.58 out of 5 average rating, 12 reviews

DisneyMansion 14 Rooms 11BR/5BA with Golf Package

RaymondRating, 5 stars35 months ago
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.
Guest favourite

Villa

5 out of 5 average rating, 79 reviews

The Golden Bear Villa | Private Pool & Theater

JaneRating, 5 starstoday
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.
Superhost

Villa

5 out of 5 average rating, 3 reviews

Beautiful Villa Champions Gate 6Beds/5Bath/Pool/Ja

SobhiRating, 5 stars8 months ago
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!
Guest favourite

Villa

5 out of 5 average rating, 20 reviews

Windsor Island Villa

JamesRating, 5 stars1 month ago
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!
Superhost

Villa

5 out of 5 average rating, 8 reviews

9BR/6BA Pool Resort Villa 5 mile to Disney #4049J

JulissaRating, 5 stars7 months ago
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

Guest favourite

Villa

4.96 out of 5 average rating, 170 reviews

4 bed villa w/private pool near Disney, sleeps 6+

DevinRating, 5 stars8 months ago
We had a great stay. The house was wonderful and close to activities. Hosts were very responsive and friendly. A++ stay. Thank you!
Guest favourite

Villa

4.83 out of 5 average rating, 77 reviews

5bedroom,pool,18min to Disney, Kissimmee davenport

FrantzRating, 5 stars1 week ago
Miguel's home was more then we expected. He communicates very well , and was also very helpful
Guest favourite

Villa

4.88 out of 5 average rating, 8 reviews

Spacious Multi Family Villa- 6Br Sunny Pool Deck!

CaressaRating, 5 stars2 months ago
We enjoyed our stay! The host was accommodating, responsive, and friendly. Clean, spacious, and worth the price. Look forward booking with them again.
Superhost

Villa

4.74 out of 5 average rating, 76 reviews

Nr Disney pool/cinema room/outdoor kitchen

AmandaRating, 5 stars7 months ago
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.
Guest favourite

Villa

5 out of 5 average rating, 24 reviews

Luxury Villa Pool/Spa 2 Masters, Highlands Reserve

MelanieRating, 5 stars1 month ago
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!
Guest favourite

Villa

4.86 out of 5 average rating, 36 reviews

South facing Modern villa in quiet gated estate

JuanaRating, 5 stars5 months ago
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!
Superhost

Villa

4.78 out of 5 average rating, 83 reviews

4-bed villa w/ beautiful pool 15 mins from Disney!

BrittniRating, 5 stars2 months ago
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
Superhost

Villa

5 out of 5 average rating, 29 reviews

Sharedale Lakeside Villa

DeannaRating, 5 stars21 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee
  6. Villa rentals