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Kissimmee Apartments & Vacation Rentals with Swimming Pool - 3023 Rentals Available.

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3,023 Vacation rentals

Filters applied: Swimming pool

(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

$95.00

Very Good (29 reviews)

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from $95.00 / night

(4)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • Min stay varies
  • 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

$165.00

Very Good (4 reviews)

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from $165.00 / night

(15)

Certificate of Excellence

1 / 38

Kissimmee Villa

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

Certificate of Excellence

$95.00

Excellent (15 reviews)

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from $95.00 / night

(13)

1 / 20

Kissimmee House

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$139.00

Very Good (13 reviews)

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from $139.00 / night

(3)

1 / 18

Kissimmee House

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

$150.00

Excellent (3 reviews)

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from $150.00 / night

(1)

1 / 33

Kissimmee Villa

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

$99.00

Excellent (1 reviews)

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from $99.00 / night

(14)

Certificate of Excellence

1 / 59

Kissimmee Villa

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

Certificate of Excellence

$70.00

Very Good (14 reviews)

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from $70.00 / night

1 / 86

Kissimmee Villa

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

$150.00

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from $150.00 / night

(7)

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

$199.00

Very Good (7 reviews)

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from $199.00 / night

(53)

1 / 64

Kissimmee House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My grandson was invited to Select 30 at ESPN. Graham told me this house was only 15 minutes away. This house is a perfect location for Disney facilities. Once out of the subdivision, you make one turn and you are at Disney. We enjoyed the pool at...”
- Review left on 08/31/2017

$114.00

Excellent (53 reviews)

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from $114.00 / night

(28)

1 / 105

Kissimmee Villa

  • 7
  • 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Nice place. Plenty of room. Just minor complaints. No big pots to cook in. Pool sticks weren't good. Just needs some small minor updates . Great area. Would stay again”
- Review left on 01/18/2018

$189.00

Very Good (28 reviews)

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from $189.00 / night

(15)

1 / 11

Kissimmee Apartment

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

$89.00

Excellent (15 reviews)

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from $89.00 / night

(26)

1 / 19

Kissimmee House

  • 4
  • 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The property was beautiful. The amenities were awesome. The property was spacious and cozy. It could use a little carpet cleaning and a few more places to hang towels. The weather was too cool for us to enjoy the pool. Was located in a great...”
- Review left on 01/05/2017

$109.00

Very Good (26 reviews)

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from $109.00 / night

(1)

1 / 47

Kissimmee Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$99.00

Excellent (1 reviews)

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from $99.00 / night

(4)

1 / 84

Kissimmee House

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

$70.00

Excellent (4 reviews)

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from $70.00 / night

(8)

Certificate of Excellence

1 / 21

Kissimmee Townhouse

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

Certificate of Excellence

$101.00

Excellent (8 reviews)

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from $101.00 / night

(15)

1 / 38

Kissimmee Villa

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$185.00

Excellent (15 reviews)

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from $185.00 / night

(1)

1 / 42

Kissimmee Apartment

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

$109.00

Excellent (1 reviews)

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from $109.00 / night

(1)

1 / 41

Kissimmee Villa

  • 7
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$376.00

Excellent (1 reviews)

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from $376.00 / night

(37)

Certificate of Excellence

1 / 75

Kissimmee House

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

Certificate of Excellence

$140.00

Excellent (37 reviews)

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from $140.00 / night

(1)

1 / 45

Kissimmee House

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

$259.00

Excellent (1 reviews)

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from $259.00 / night

1 / 19

Kissimmee House

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

$150.00

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from $150.00 / night

(10)

1 / 12

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

$75.00

Excellent (10 reviews)

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from $75.00 / night

(23)

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

$130.00

Excellent (23 reviews)

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from $130.00 / night

(86)

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

$75.00

Very Good (86 reviews)

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from $75.00 / night

(42)

1 / 36

Kissimmee House

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

$150.00

Excellent (42 reviews)

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from $150.00 / night

(3)

1 / 19

Kissimmee House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“What a lovely home. We stayed here for 9 nights. The house had everything we needed and was well equipped. The beds were very comfortable. The pool was refreshing after a long day visiting Disney or Universal. We loved the view of the lake with the...”
- Review left on 05/22/2016

$70.00

Excellent (3 reviews)

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from $70.00 / night

(9)

Certificate of Excellence

1 / 98

Kissimmee Villa

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

Certificate of Excellence

$160.00

Very Good (9 reviews)

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from $160.00 / night

(4)

1 / 71

Kissimmee Villa

  • 7
  • 16
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$160.00

Excellent (4 reviews)

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from $160.00 / night

1 / 26

Kissimmee Villa

  • 10
  • 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$526.00

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from $526.00 / night

(3)

1 / 22

Kissimmee Villa

  • 5
  • 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“10 of my family stayed at this Villa. It was perfect so much space. The villa is very well equipped with everything you could possibly need Thank you for a wonderful holiday”
- Review left on 07/11/2016

$165.00

Excellent (3 reviews)

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from $165.00 / night

(9)

1 / 44

Kissimmee House

  • 8
  • 24
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We absolutely loved this vacation home and would definitely go back! All adult rooms had king size beds and were very comfortable. The variety of different themed rooms were so fun and well thought out with so many things in each room to do....”
- Review left on 06/15/2016

$399.00

Excellent (9 reviews)

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from $399.00 / night

(3)

1 / 118

Kissimmee House

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

$70.00

Very Good (3 reviews)

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from $70.00 / night

(1)

1 / 37

Kissimmee Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$89.00

Excellent (1 reviews)

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from $89.00 / night

(5)

1 / 22

Kissimmee Villa

  • 6
  • 13
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$195.00

Excellent (5 reviews)

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from $195.00 / night

(54)

1 / 51

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Thank you for allowing us to stay at your beautiful home this week! Everything was perfect! It was clean, had everything we needed and was convenient to every place we needed to go. Would definitely recommend to anyone needing a place to stay close...”
- Review left on 06/24/2017

$125.00

Excellent (54 reviews)

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from $125.00 / night

(9)

1 / 16

Kissimmee Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$62.00

Excellent (9 reviews)

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from $62.00 / night

1 / 21

Kissimmee Townhouse

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

$39.00

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from $39.00 / night

1 / 22

Kissimmee Apartment

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

$69.00

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from $69.00 / 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

$80.00

Very Good (14 reviews)

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from $80.00 / night