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Kissimmee Apartments & Vacation Rentals with Swimming Pool - 1373 Rentals Available.

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1,373 Vacation rentals

Filters applied: Swimming pool

(11)

1 / 33

Kissimmee House

  • 8
  • 22
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$310.00

Excellent (11 reviews)

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from $310.00 / night

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(79)

1 / 51

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 48 minutes

“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 (79 reviews)

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from $144.00 / night

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(23)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
“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
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool

$98.00

Average (8 reviews)

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from $98.00 / night

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(6)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 40 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 (6 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. 3 hours 2 minutes

$91.00

Excellent (3 reviews)

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from $91.00 / night

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(55)

1 / 27

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
“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 (55 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. 3 hours 13 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 2 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

$121.00

Very Good (14 reviews)

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from $121.00 / night

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(9)

1 / 45

Kissimmee House

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

$114.00

Very Good (9 reviews)

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from $114.00 / night

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(22)

1 / 48

Kissimmee Villa

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

Responds fast! Avg. 1 hour 43 minutes

“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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(1)

1 / 47

Kissimmee Villa

  • 7
  • 14
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
“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 15 minutes

$126.00

Excellent (17 reviews)

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from $126.00 / 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 52 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 15 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
  • 12
  • 7 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

$252.00

Very Good (13 reviews)

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from $252.00 / 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

$155.00

Excellent (27 reviews)

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from $155.00 / 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. 3 hours 46 minutes

$86.00

Excellent (4 reviews)

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from $86.00 / night

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(4)

1 / 27

Kissimmee Villa

  • 5
  • 11
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 115 mi
  • Swimming pool

$149.00

Very Good (4 reviews)

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from $149.00 / night

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(15)

1 / 59

Kissimmee Villa

  • 4
  • 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 44 minutes

$92.00

Very Good (15 reviews)

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from $92.00 / night

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(60)

1 / 41

Kissimmee House

  • 4
  • 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 125 mi
  • Swimming pool

Responds fast! Avg. 3 hours 12 minutes

“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

$194.00

Excellent (60 reviews)

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from $194.00 / night

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(55)

1 / 30

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$102.00

Very Good (55 reviews)

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from $102.00 / night

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(7)

1 / 47

Kissimmee House

  • 3
  • 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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 (7 reviews)

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from $132.00 / night

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(51)

1 / 70

Kissimmee House

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

Responds fast! Avg. 2 hours 53 minutes

“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 (51 reviews)

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from $172.00 / night

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(15)

1 / 28

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$114.00

Excellent (15 reviews)

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from $114.00 / night

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(8)

1 / 57

Kissimmee House

  • 9
  • 24
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Swimming pool

Responds fast! Avg. 3 hours 11 minutes

“Our family vacation was wonderful! The house was beautiful, very well decorated, and spacious, it was everything we expected and much-much more. We enjoyed sitting outside on the screened in patio and outdoor furniture, the pool, and hot tub every...”
- Review left on 05/02/2018

$367.00

Excellent (8 reviews)

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from $367.00 / night

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(7)

1 / 19

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Awesome and beautiful time spent at the Kennedy #5. The owner Dian such a caring person. The house was very clean. All of the beds in the home was so comfortable we all slept soundly. The pool was excellent and the lake view was the most beautiful...”
- Review left on 08/08/2021

$114.00

Excellent (7 reviews)

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from $114.00 / 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. 3 hours 44 minutes

$92.00

Excellent (5 reviews)

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from $92.00 / night

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(3)

1 / 27

Kissimmee Condo

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“**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
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$229.00

Very Good (9 reviews)

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from $229.00 / night

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(3)

1 / 41

Kissimmee Villa

  • 7
  • 18
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
“This is a big house! Three families would have no problems here and plently of space not to be under each others feet. Close to Disney and main route to all the normal popular attractions. House was clean and tidy, kitchen had everything should you...”
- Review left on 04/20/2015

$188.00

Excellent (3 reviews)

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from $188.00 / night

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(3)

1 / 63

Kissimmee House

  • 8
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 2 minutes

$344.00

Very Good (3 reviews)

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from $344.00 / night

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(17)

1 / 31

Kissimmee Villa

  • 7
  • 15
  • 4 nights min
  • Nearest beach 112 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 49 minutes

“the home was all that and more, the only dissatisfaction was the games were not working but the kids were still enterained”
- Review left on 08/11/2016

$258.00

Excellent (17 reviews)

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from $258.00 / night

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(11)

1 / 16

Kissimmee Condo

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 46 minutes

“My family and I stayed at this place for a week. We loves it the house is super clean it's close to every disney park the pool was really clean too. The only thing we didn't like was the parking spot every nigth when we got home we had to park on the...”
- Review left on 06/29/2016

$74.00

Excellent (11 reviews)

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from $74.00 / night

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(10)

1 / 108

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Nearest beach 81 mi
  • Swimming pool
  • Child friendly

$184.00

Very Good (10 reviews)

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from $184.00 / night

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(3)

1 / 19

Kissimmee Villa

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

Responds fast! Avg. 3 hours 29 minutes

$109.00

Very Good (3 reviews)

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from $109.00 / night

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