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Kissimmee Apartments & Vacation Rentals with Swimming Pool - 3170 Rentals Available.

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3,170 Vacation rentals

Filters applied: Swimming pool

(71)

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 (71 reviews)

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from $144.00 / night

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(8)

1 / 27

Kissimmee House

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

Responds fast! Avg. 1 hour 33 minutes

$102.00

Average (8 reviews)

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from $102.00 / night

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(23)

1 / 28

Kissimmee Townhouse

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

Responds fast! Avg. 1 hour 33 minutes

“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

$102.00

Excellent (23 reviews)

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from $102.00 / night

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(11)

1 / 33

Kissimmee House

  • 6
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 32 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

$217.00

Excellent (11 reviews)

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from $217.00 / night

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(53)

1 / 27

Kissimmee Townhouse

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

Responds fast! Avg. 1 hour 33 minutes

“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

$102.00

Very Good (53 reviews)

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from $102.00 / night

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(3)

1 / 23

Kissimmee Apartment

  • 3
  • 8
  • min stay varies
  • 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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(4)

1 / 41

Kissimmee Apartment

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

$114.00

Very Good (4 reviews)

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from $114.00 / 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 44 minutes

$233.00

Excellent (5 reviews)

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from $233.00 / night

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(4)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 23 minutes

“We had a wonderful time at this home. The house is spotless and the bedrooms are all very comfortable. The pool is lovely and we also took advantage of having access to the huge clubhouse pool . The commute to Disney was easy and quick. The owner...”
- Review left on 05/16/2016

$224.00

Very Good (4 reviews)

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from $224.00 / night

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(28)

1 / 20

Kissimmee Villa

  • 3
  • 8
  • 3 nights min
  • Nearest beach 104 mi
  • Swimming pool
  • Child friendly
“Was in a great Location close to dining, shopping and attractions. A little further from the beach then expected, but the neighborhood was quite and the house was bigger than expected. A perfect house for a family to stay in...”
- Review left on 09/26/2016

$115.00

Very Good (28 reviews)

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from $115.00 / night

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(43)

1 / 43

Kissimmee House

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

Responds fast! Avg. 2 hours 29 minutes

“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

$172.00

Excellent (43 reviews)

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from $172.00 / 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 43 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

$104.00

Very Good (14 reviews)

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from $104.00 / night

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(17)

1 / 38

Kissimmee Villa

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

Responds fast! Avg. 1 hour 25 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
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 28 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

$109.00

Average (4 reviews)

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from $109.00 / 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

$155.00

Excellent (1 reviews)

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from $155.00 / night

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(4)

1 / 30

Kissimmee Villa

  • 7
  • 16
  • 3 nights min
  • Nearest beach 90 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

$224.00

Excellent (4 reviews)

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from $224.00 / night

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(17)

Certificate of Excellence

1 / 42

Kissimmee House

  • 8
  • 18
  • min stay varies
  • Nearest beach 56 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 23 minutes

Certificate of Excellence

“This vacation home is absolutely beautiful! It looks identical to the pictures on the website. We stayed at the Reunion Emperor in March 2017 for a total of 8 nights. Our group consisted of 6 adults and 7 children - three families all under one...”
- Review left on 01/20/2018

$263.00

Excellent (17 reviews)

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from $263.00 / night

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(8)

Certificate of Excellence

1 / 45

Kissimmee House

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

Certificate of Excellence

“All around great stay. Bob and Diane were extremely helpful. Would highly recommend them for your vacation needs...”
- Review left on 07/29/2018

$92.00

Excellent (8 reviews)

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from $92.00 / night

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(3)

1 / 18

Kissimmee House

  • 8
  • 19
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$228.00

Excellent (3 reviews)

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from $228.00 / night

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(21)

Certificate of Excellence

1 / 48

Kissimmee Villa

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

Responds fast! Avg. 1 hour 20 minutes

Certificate of Excellence

“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 (21 reviews)

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from $228.00 / night

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(13)

1 / 26

Kissimmee House

  • 7
  • 15
  • min stay varies
  • 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

$172.00

Very Good (13 reviews)

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from $172.00 / 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. 35 minutes

$75.00

Excellent (4 reviews)

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from $75.00 / night

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1 / 86

Kissimmee Villa

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

Responds fast! Avg. 1 hour 25 minutes

$172.00

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from $172.00 / night

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(11)

1 / 25

Kissimmee Townhouse

  • 3
  • 7
  • min stay varies
  • 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 (11 reviews)

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from $70.00 / night

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(8)

1 / 23

Kissimmee Villa

  • 8
  • 19
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“this is a very nice home for big families and is very short drive to Disney world would stay there again”
- Review left on 12/05/2016

$228.00

Very Good (8 reviews)

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from $228.00 / night

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(10)

Certificate of Excellence

1 / 2

Kissimmee Villa

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

Responds fast! Avg. 36 minutes

Certificate of Excellence

“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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(25)

Certificate of Excellence

1 / 64

Kissimmee Villa

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

Responds fast! Avg. 3 hours 20 minutes

Certificate of Excellence

“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 (25 reviews)

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from $138.00 / night

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(1)

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

$229.00

Excellent (1 reviews)

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from $229.00 / night

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(89)

1 / 102

Kissimmee Townhouse

  • 3
  • 8
  • 3 nights min
  • 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

$86.00

Excellent (89 reviews)

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from $86.00 / night

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1 / 18

Kissimmee House

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

$229.00

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from $229.00 / night

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(13)

1 / 20

Kissimmee House

  • 5
  • 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 12 minutes

“This finely appointed home provided just the oasis we needed after busy days at the parks and shopping spots of Orlando. Home is spacious, clean, well decorated. The beds were super comfy, lots of linens at our disposal. The pool and hot tub...”
- Review left on 01/01/2017

$171.00

Very Good (13 reviews)

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from $171.00 / night

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(4)

1 / 22

Kissimmee House

  • 6
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house is extremely comfortable and accommodating. We had 6 adults and 3 children and there was plenty of room. The home is very clean overall and had lots of the essentials. For anything extra you may need there are tons of local shopping...”
- Review left on 11/17/2017

$172.00

Excellent (4 reviews)

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from $172.00 / night

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(4)

1 / 18

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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(15)

1 / 59

Kissimmee Villa

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

Responds fast! Avg. 35 minutes

$81.00

Very Good (15 reviews)

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from $81.00 / night

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(7)

Certificate of Excellence

1 / 25

Kissimmee House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 20 minutes

Certificate of Excellence

“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

$113.00

Very Good (7 reviews)

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from $113.00 / night

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(35)

1 / 19

Kissimmee House

  • 4
  • 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a last minute vacation opportunity and Sheryl was so accommodating and excellent and we loved her place! We had 5 kids and 2 adults and there was tons of space to relax and have private space. The pool was amazing!! It was the perfect temp and...”
- Review left on 07/07/2018

$137.00

Very Good (35 reviews)

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from $137.00 / night

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(57)

Certificate of Excellence

1 / 41

Kissimmee House

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

Responds fast! Avg. 1 hour 33 minutes

Certificate of Excellence

“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 (57 reviews)

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from $144.00 / night

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(11)

Certificate of Excellence

1 / 22

Kissimmee Villa

  • 6
  • 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 49 minutes

Certificate of Excellence

$224.00

Excellent (11 reviews)

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from $224.00 / night

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(6)

1 / 37

Kissimmee House

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

Responds fast! Avg. 3 hours 7 minutes

“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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1 / 22

Kissimmee Apartment

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 18 minutes

$80.00

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from $80.00 / night

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