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Kissimmee Apartments & Vacation Rentals with Swimming Pool - 2057 Rentals Available.

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2,057 Vacation rentals

Filters applied: Swimming pool

(11)

1 / 33

Kissimmee House

  • 8
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 29 minutes

“We loved this home and would definitely book it again when traveling with a large group. Whether you have a toddler or a teenager in your group, this house has everything you?ll need. The pool is awesome and the house was very clean. The location is...”
- Review left on 10/13/2019

$264.00

Excellent (11 reviews)

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from $264.00 / night

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(75)

1 / 51

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“This home was perfect for us just as it has been for previous stays. We keep coming back to this wonderful home because it accommodates us so well. Thank you again for letting us call this house home for another week...”
- Review left on 02/18/2019

$144.00

Excellent (75 reviews)

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from $144.00 / night

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(23)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The location is perfect for a Disney vacation. You can't get much closer to DisneyWorld without staying onsite. I prefer to stay offsite whenever we visit, because it's nice to be able to "escape" from all the Disney magic every now and then. The...”
- Review left on 10/27/2017

$98.00

Excellent (23 reviews)

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from $98.00 / night

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(8)

1 / 27

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

$98.00

Average (8 reviews)

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from $98.00 / night

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(5)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 39 minutes

“This home was beautiful and clean better than what we thought. The home was conveniently located near shopping centers...”
- Review left on 12/29/2019

$224.00

Very Good (5 reviews)

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from $224.00 / night

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(3)

1 / 23

Kissimmee Apartment

  • 3
  • 8
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

$91.00

Excellent (3 reviews)

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from $91.00 / night

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(54)

1 / 27

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The accommodations were excellent, all the amenities required for a comfortable stay, the place was very clean, the HVAC worked fine no issues. I recommend staying here to anyone. Than you for everything Manny and Carmen we will be back soon...”
- Review left on 01/23/2017

$98.00

Very Good (54 reviews)

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from $98.00 / night

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(43)

1 / 43

Kissimmee House

  • 4
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Great location. Near Disney and shops. The owner were very nice ? called to see if everything is o.k, and agreed to a late departure. The view of the lake is wonderful and the pool is great. The kids rooms upstairs was the one thing I liked less....”
- Review left on 10/17/2018

$180.00

Excellent (43 reviews)

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from $180.00 / night

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(5)

1 / 50

Kissimmee House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 34 minutes

$233.00

Excellent (5 reviews)

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from $233.00 / night

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(14)

1 / 40

Kissimmee Apartment

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 19 minutes

“Great value for your money. The condo was very clean. I was really impressed with the unit. There was plenty of space for everyone to spread out and enjoy themselves. It was well stocked with linen. The washer and dryer worked great. Unit has a...”
- Review left on 04/30/2015

$98.00

Very Good (14 reviews)

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from $98.00 / night

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(9)

1 / 45

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“All around great stay. Bob and Diane were extremely helpful. Would highly recommend them for your vacation needs...”
- Review left on 07/29/2018

$104.00

Very Good (9 reviews)

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from $104.00 / night

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(22)

Certificate of Excellence

1 / 48

Kissimmee Villa

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 21 minutes

Travelers’ Choice award

“This house is everything the ad states and more!! The location is perfect and is so conveniently located to Disney, fantastic mini putts, a beautiful golf course, and restaurants. The lay out of the house is fantastic allowing everyone in your party...”
- Review left on 03/05/2018

$228.00

Excellent (22 reviews)

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from $228.00 / night

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(4)

1 / 50

Kissimmee Villa

  • 7
  • 16
  • 3 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly
“The location is great. Close to all the parks. Restaurants and grocery right up the street. The house was fabulous. We had 14 people stay in the house, plenty of room. The pool and hot tub were used every night...”
- Review left on 11/25/2014

$115.00

Excellent (4 reviews)

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from $115.00 / night

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(4)

1 / 41

Kissimmee Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 40 minutes

$114.00

Very Good (4 reviews)

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from $114.00 / night

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(1)

1 / 47

Kissimmee Villa

  • 7
  • 14
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“Location, location, location! This well- equipped neat, spacious and cozy luxury home is close to everything you'd ever want to do in Orlando,Florida. Children open the patio doors and they are in their own pool, while the family relax in or out of...”
- Review left on 03/22/2016

$188.00

Excellent (1 reviews)

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from $188.00 / night

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(17)

1 / 38

Kissimmee Villa

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 38 minutes

$109.00

Excellent (17 reviews)

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from $109.00 / night

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(4)

1 / 23

Kissimmee Villa

  • 4
  • 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 44 minutes

“From the time we viewed this beautiful home on the website, we knew this was the place we wanted to celebrate our 2nd. Anniversary here. This place is decorated with a touch of sophistication and elegance yet it made you feel at home once you walked...”
- Review left on 10/07/2015

$129.00

Average (4 reviews)

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from $129.00 / night

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1 / 94

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 113 mi
  • Swimming pool

Responds fast! Avg. 3 hours 38 minutes

$172.00

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from $172.00 / night

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(12)

1 / 25

Kissimmee Townhouse

  • 3
  • 7
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“Will recommended to friends when they are planning to go Orlando in July/August.Closed to Disney world, shopping centres, etc...”
- Review left on 04/18/2016

$70.00

Excellent (12 reviews)

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from $70.00 / night

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(13)

1 / 26

Kissimmee House

  • 7
  • 15
  • 10 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Our stay was just breathtaking. The best stay ever! For most of us it was our first time experiencing a Vacation home and they definitely suggest to come back again! Everything was in place , everything was clean and well taken care of, the pool was...”
- Review left on 09/12/2017

$264.00

Very Good (13 reviews)

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from $264.00 / night

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(7)

1 / 25

Kissimmee House

  • 4
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 57 minutes

“We were quite happy with our stay. The house was clean and comfortable. The pool however was not cleaned prior to us coming so we were unable to use it out first week. They came and cleaned it after calling about it. The area was also quiet and...”
- Review left on 08/02/2018

$121.00

Very Good (7 reviews)

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from $121.00 / night

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(27)

1 / 64

Kissimmee Villa

  • 4
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My wife and I had an enjoyable, relaxing 8 week stay at the villa this past winter and were impressed with the cleanliness while the neighborhood itself is quiet and serene. We were close to a local park with basketball and tennis courts along with...”
- Review left on 03/28/2016

$138.00

Excellent (27 reviews)

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from $138.00 / night

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(2)

1 / 56

Kissimmee Villa

  • 8
  • 18
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“We had the best vacation ever and this property was everything a family my size needed and more.. I will recommend this to anyone that I come in contact with because it was so comfortable,convenient,spacious,nicely decorated and it was not far from...”
- Review left on 04/07/2016

$306.00

Average (2 reviews)

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from $306.00 / night

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(4)

1 / 118

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 33 minutes

$75.00

Excellent (4 reviews)

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from $75.00 / night

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(4)

1 / 2

Kissimmee Villa

  • 5
  • 11
  • min stay varies
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly

$125.00

Very Good (4 reviews)

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from $125.00 / night

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(10)

1 / 40

Kissimmee Villa

  • 6
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 120 mi
  • Swimming pool

Responds fast! Avg. 19 minutes

“We went with two families and everyone loved the place! It was close to Disney. Relaxing in the hot tub after a day a Disney was perfect...”
- Review left on 12/23/2017

$229.00

Excellent (10 reviews)

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from $229.00 / night

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(15)

1 / 59

Kissimmee Villa

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 24 minutes

$81.00

Very Good (15 reviews)

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from $81.00 / night

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(59)

Certificate of Excellence

1 / 41

Kissimmee House

  • 4
  • 8
  • 3 nights min
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 8 minutes

Travelers’ Choice award

“A well equipped, well maintained vacation home. Plenty of room for our group of 4 adults and 3 children. The private pool was great. This was our first experience renting a whole house. We enjoyed our stay...”
- Review left on 03/31/2018

$144.00

Excellent (59 reviews)

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from $144.00 / night

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(55)

1 / 30

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Clean, beautiful and all you need to feel in home, close to parks, restaurants and everything, I will stay here again, Thanks to Harish and Jaya...”
- Review left on 05/28/2017

$86.00

Very Good (55 reviews)

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from $86.00 / night

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(89)

1 / 102

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The location was convenient as stated to all the parks. It was a safe gated complex. The fact that we had 3 bedrooms and bathrooms enabled us to get ready and out the door easily to the parks. The kitchen was great for breakfast and making lunch to...”
- Review left on 01/30/2018

$68.00

Excellent (89 reviews)

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from $68.00 / night

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(12)

1 / 19

Kissimmee Villa

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 56 minutes

“Accommodation was perfect. We wanted a relaxing weekend getaway and this home more than exceeded our expectations. We will definitely book this house again...”
- Review left on 09/19/2017

$115.00

Very Good (12 reviews)

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from $115.00 / night

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(6)

1 / 47

Kissimmee House

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“I was here from 1/29-2/26 and the stay was awesome. The house was everything that was advertised and the pictures were right on. The house was very clean and equipped with all the thing a person needs to enjoy a month in sunny Orlando. We didn't...”
- Review left on 02/27/2017

$132.00

Excellent (6 reviews)

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from $132.00 / night

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(50)

Certificate of Excellence

1 / 75

Kissimmee House

  • 4
  • 8
  • 5 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 50 minutes

Travelers’ Choice award

“This house was the perfect setting for our Disney vacation! Each young person in our group of 5 enjoyed having the privacy of having their own bedroom and bathroom. The house was extremely clean, well-equipped and convenient to all! Although we...”
- Review left on 07/13/2018

$172.00

Excellent (50 reviews)

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from $172.00 / night

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(15)

1 / 28

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The property is perfect. The pictures don't do the pool justice. It is one of the nicest pools you'll see on a vacation property. We had 3 children all 3 and under and it was no problem at all. The drive to Disney was a very quick and easy drive and...”
- Review left on 12/02/2017

$104.00

Excellent (15 reviews)

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from $104.00 / night

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(3)

1 / 41

Kissimmee House

  • 6
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$401.00

Excellent (3 reviews)

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from $401.00 / night

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(2)

1 / 49

Kissimmee House

  • 6
  • 16
  • min stay varies
  • Nearest beach 114 mi
  • Swimming pool
  • Child friendly
“We loved our recent trip to Florida with family. Some flew in and some drove. We loved the nice and clean big house with lots of space for everyone to retreat to if they wanted. The pool was great and very well used for the 10 days we were there. We...”
- Review left on 03/24/2016

$295.00

Excellent (2 reviews)

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from $295.00 / night

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(6)

1 / 19

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This vacation was a winner and Bob and Dianne provided us with a fantastic and welcoming vacation home rental. It was so peaceful and relaxing. The home was very clean and well maintained. I would strongly recommend this property to anyone visiting...”
- Review left on 05/13/2018

$98.00

Excellent (6 reviews)

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from $98.00 / night

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(5)

1 / 84

Kissimmee House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 24 minutes

$81.00

Excellent (5 reviews)

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from $81.00 / night

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(3)

1 / 27

Kissimmee Condo

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“**I made the contact and found this condo for my daughter that is active duty Military, the following were her comments on the the rental: Lots of room, owner was very helpful with information, answered emails quickly. Easy deal on short notice....”
- Review left on 09/27/2016

$86.00

Excellent (3 reviews)

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from $86.00 / night

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(9)

1 / 19

Kissimmee House

  • 5
  • 12
  • 10 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house the perfect size for my family. The pool was great. The game room was awesome and had great games. Overall one of the best rental homes you can get...”
- Review left on 11/25/2017

$258.00

Very Good (9 reviews)

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from $258.00 / night

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