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Kissimmee Apartments & Vacation Rentals with Swimming Pool - 384 Rentals Available.

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384 Vacation rentals

Filters applied: Swimming pool

(23)

1 / 105

Kissimmee Villa

  • 7
  • 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We took our family of 20, including 12 grandchildren, to the Disney Orlando area this month. This house we rented worked pretty well for us but there are things that could have been better. I would give it a 3 1/2 rating. I would not say that it...”
- Review left on 06/24/2016

$149

Very Good (23 reviews)

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from $149 / night

(8)

Certificate of Excellence

1 / 21

Kissimmee Townhouse

  • 3
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

$100

Excellent (8 reviews)

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from $100 / night

(5)

1 / 19

Kissimmee House

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“For 7 guys on a golf trip this house was exactly what we needed. There were 7 beds, along with 2 pull out couches, giving us plenty of beds. Four bathrooms made getting ready to play golf or to go out to dinner was very easy. The pool and hot tub...”
- Review left on 01/20/2017

$100

Very Good (5 reviews)

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from $100 / night

(7)

1 / 33

Kissimmee House

  • 6
  • 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We've stayed in a lot of vacation homes in this area over the last 20 years and I have to say that this was one of the best equipped that we've ever stayed in. The house has been recently renovated and everything was very nice and clean. The pool is...”
- Review left on 03/11/2017

$149

Excellent (7 reviews)

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from $149 / night

(14)

1 / 34

Kissimmee Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“This is a very clean & well kept house, in a secure neighborhood. My children had great time in the covered swimming pool in the back yard. I will highly recommend this house to feel at home when you are away from your home...”
- Review left on 12/31/2016

$157

Excellent (14 reviews)

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from $157 / night

(17)

1 / 18

Kissimmee Villa

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We used the home for 4 days during the Halloween season. It was very clean and well maintained. Easy access to all of the area attractions made this the perfect location for our needs. I would highly recommend this property...”
- Review left on 10/21/2015

$100

Very Good (17 reviews)

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from $100 / night

(3)

1 / 29

Kissimmee Villa

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

$185

Very Good (3 reviews)

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from $185 / night

(15)

1 / 24

Kissimmee Villa

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“My wife & I have rented homes in Europe ( not a good experience ) & once in USA. ( This one was not even what was advertised ). So you can imagine we were somewhat apprehensive as to what we were going to get for our 10 day stay. This is the real...”
- Review left on 03/13/2017

$143

Excellent (15 reviews)

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from $143 / night

(1)

1 / 45

Kissimmee House

  • 8
  • 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$289

Excellent (1 reviews)

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from $289 / night

(35)

1 / 50

Kissimmee House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“House really is only 5min from Disney parks and perfect for a family vacation. Pool and hot tub were perfect for mid day break and refresh from the park. Had an issue with the dryer on day 2, owner Simon promptly replaced it with a new one. He was...”
- Review left on 05/02/2016

$99

Very Good (35 reviews)

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from $99 / night

1 / 33

Kissimmee Villa

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

$79

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from $79 / night

(8)

1 / 26

Kissimmee House

  • 7
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Everything at the house was perfect. Clean and running properly. Kids were kept busy with game systems and pool tables. Wish there were more selection of bigger sauce pots. But other then that no complaints...”
- Review left on 08/11/2015

$180

Very Good (8 reviews)

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from $180 / night

(42)

1 / 36

Kissimmee House

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

$150

Excellent (42 reviews)

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from $150 / night

(45)

1 / 64

Kissimmee House

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

$114

Excellent (45 reviews)

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from $114 / night

(5)

1 / 20

Kissimmee House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“This house was absolutely amazing! Being able to wake up and have breakfast or coffee poolside overlooking the lake was a refreshing way to begin each day of adventures. Ending each day with a relaxing dip in the pool/hot tub was just as nice. Bob...”
- Review left on 07/24/2017

$69

Excellent (5 reviews)

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from $69 / night

(19)

1 / 16

Kissimmee Villa

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The home was clean & spacious. There was no gas in the grill although the contract stated the renters were responsible for filling. For a home that sleeps 16 it needs more towels & wash clothes. Very comfortables beds & good amenities. Would stay...”
- Review left on 03/06/2017

$143

Excellent (19 reviews)

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from $143 / night

(8)

1 / 48

Kissimmee Villa

  • 5
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 116 mi
  • Swimming pool
“Over all,This was a beautiful home. We had a great time visiting Fla. This home is very close to all the attractions we had planed to visit. All within 20 min. or so. Let me tell you about the home, I was very happy when I walked in the door. The...”
- Review left on 10/12/2016

$157

Excellent (8 reviews)

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from $157 / night

(21)

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

$120

Excellent (21 reviews)

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from $120 / night

1 / 25

Kissimmee Villa

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

$169

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from $169 / night

(4)

1 / 29

Kissimmee Villa

  • 6
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The home was very clean and beautiful, and exactly what was advertised. The rooms and amenities were all there as described. We were very happy with the home and the neighborhood. It was close to Disney, stores and major highways. If you are...”
- Review left on 06/11/2016

$185

Excellent (4 reviews)

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from $185 / night

1 / 9

Kissimmee Villa

  • 6
  • 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$240

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from $240 / night

(14)

1 / 38

Kissimmee Villa

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

$95

Excellent (14 reviews)

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from $95 / night

(21)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“My family love the house very spacious, clean, convenient location to all the parks , restaurants and outlet stores. Overall I will definitely rent again on the same location...”
- Review left on 08/09/2016

$79

Excellent (21 reviews)

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from $79 / night

(5)

1 / 32

Kissimmee Villa

  • 6
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The home was clean and spacious. My daughter loved the décor and took pictures so that she can replicate it. There was a leak in the faucet so I called the repairman. He was polite and responsive. When he was unable to repair it so he went out...”
- Review left on 05/26/2016

$199

Very Good (5 reviews)

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from $199 / night

1 / 23

Kissimmee House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $105 / night

(14)

1 / 33

Kissimmee Apartment

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$75

Very Good (14 reviews)

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from $75 / night

(13)

1 / 11

Kissimmee Apartment

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

$89

Excellent (13 reviews)

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from $89 / night

(2)

1 / 100

Kissimmee House

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

$68

Excellent (2 reviews)

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from $68 / night

1 / 41

Kissimmee Apartment

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

$135

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from $135 / night

1 / 21

Kissimmee Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $170 / night

(29)

1 / 12

Kissimmee Villa

  • 4
  • 8
  • 4 nights min
  • Nearest beach 105 mi
  • Swimming pool
  • Child friendly
“We had an awesome time and the owner was a pleasure also the property manager was awesome and prompt. Beautiful home spacious and clean. Convienant to all atractions”
- Review left on 12/20/2016

$100

Very Good (29 reviews)

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from $100 / night

(6)

1 / 24

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

$169

Very Good (6 reviews)

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from $169 / night

(35)

Certificate of Excellence

1 / 75

Kissimmee House

  • 4
  • 8
  • Min stay varies
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Certificate of Excellence

$135

Excellent (35 reviews)

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from $135 / night

(1)

1 / 47

Kissimmee Apartment

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$79

Excellent (1 reviews)

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from $79 / night

(26)

1 / 20

Kissimmee Townhouse

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We really enjoyed our stay and everything was very clean and well taken care of. Only suggestion would be to maybe replace couches in living room as they are very worn out...”
- Review left on 01/13/2017

$65

Very Good (26 reviews)

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from $65 / night

(84)

1 / 102

Kissimmee Townhouse

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house is the same as the photos show. Food, near supermarket, excellent treatment to rent. I'll go back and rent the same house. Thank you”
- Review left on 10/17/2016

$65

Very Good (84 reviews)

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from $65 / night

(1)

1 / 51

Kissimmee Apartment

  • 1
  • 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$65

Excellent (1 reviews)

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from $65 / night

(6)

1 / 19

Kissimmee Villa

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“This place was more than enough room for the 6 of us. House had everything needed for a weeks stay, from linen to appliances to to prepare and make nightly meals. If I had to change anything I would equipped the smaller three bedrooms with overhead...”
- Review left on 07/20/2016

$100

Excellent (6 reviews)

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from $100 / night

(3)

1 / 62

Kissimmee House

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

$39

Excellent (3 reviews)

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from $39 / night

(4)

1 / 33

Kissimmee Apartment

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

$65

Very Good (4 reviews)

Inquire

from $65 / night