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Kissimmee Apartments & Vacation Rentals with Swimming Pool - 503 Rentals Available.

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503 Vacation rentals

Filters applied: Swimming pool

(4)

1 / 20

Kissimmee House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“The Kennedy 1 has everything you need to enjoy a family vacation. Bob and Diane were easy to book with and to get in contact with during our stay. The house comes equipped with everything you need and is a 10 minutes drive away from restaurants...”
- Review left on 08/06/2016

$75

Excellent (4 reviews)

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from $75 / 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

(33)

1 / 75

Kissimmee House

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

$140

Excellent (33 reviews)

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from $140 / night

(43)

1 / 64

Kissimmee House

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

$122

Excellent (43 reviews)

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from $122 / night

(6)

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 (6 reviews)

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from $180 / night

(8)

Certificate of Excellence

1 / 21

Kissimmee Townhouse

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

Certificate of Excellence

$48

Excellent (8 reviews)

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from $48 / night

1 / 57

Kissimmee House

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

$122

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from $122 / night

(23)

1 / 44

Kissimmee House

  • 7
  • 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$250

Excellent (23 reviews)

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from $250 / 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

(5)

1 / 33

Kissimmee Apartment

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

$70

Excellent (5 reviews)

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from $70 / night

(50)

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

$79

Very Good (50 reviews)

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from $79 / night

(5)

Certificate of Excellence

1 / 37

Kissimmee Villa

  • 8
  • 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 138 mi
  • Swimming pool

Certificate of Excellence

$299

Excellent (5 reviews)

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from $299 / night

(12)

1 / 11

Kissimmee Apartment

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

$89

Excellent (12 reviews)

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from $89 / night

(2)

1 / 26

Kissimmee Townhouse

  • 3
  • 8
  • 1 night min
  • Nearest beach 116 mi
  • Swimming pool
  • Child friendly

$48

Average (2 reviews)

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from $48 / night

(2)

1 / 100

Kissimmee House

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

$65

Excellent (2 reviews)

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from $65 / 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

1 / 41

Kissimmee House

  • 6
  • 14
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly

$150

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from $150 / night

(1)

1 / 28

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

$75

Excellent (1 reviews)

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from $75 / night

(26)

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 (26 reviews)

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from $100 / night

(2)

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

$180

Very Good (2 reviews)

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from $180 / night

(13)

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

Very Good (13 reviews)

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from $80 / night

(41)

1 / 36

Kissimmee House

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

$150

Excellent (41 reviews)

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from $150 / 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

(12)

1 / 24

Kissimmee House

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

$109

Very Good (12 reviews)

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from $109 / night

1 / 86

Kissimmee Villa

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

$150

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from $150 / night

1 / 30

Kissimmee Villa

  • 7
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$230

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from $230 / night

(1)

1 / 37

Kissimmee Apartment

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

$89

Excellent (1 reviews)

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from $89 / night

(15)

1 / 34

Kissimmee Villa

  • 7
  • 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$250

Excellent (15 reviews)

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from $250 / night

(2)

1 / 37

Kissimmee House

  • 6
  • 14
  • 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

$245

Excellent (2 reviews)

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from $245 / night

1 / 18

Kissimmee House

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

$200

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from $200 / night

(1)

1 / 52

Kissimmee Villa

  • 7
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“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

$164

Excellent (1 reviews)

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from $164 / night

(1)

1 / 41

Kissimmee Villa

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

$375

Excellent (1 reviews)

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from $375 / night

(10)

1 / 41

Kissimmee Villa

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

$175

Excellent (10 reviews)

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from $175 / night

(7)

Certificate of Excellence

1 / 98

Kissimmee Villa

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

Certificate of Excellence

$150

Very Good (7 reviews)

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from $150 / night

(1)

1 / 42

Kissimmee Apartment

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

$99

Excellent (1 reviews)

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from $99 / night

1 / 41

Kissimmee House

  • 5
  • 11
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $200 / night

(2)

1 / 27

Kissimmee Villa

  • 5
  • 10
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We were three moms with each two girls with ages ranging from 7-12. The house was very comfortable and close to all the attractions. On our off days we relaxed inside while the kids played in the pool. The house is big enough and no one got in each...”
- Review left on 08/09/2011

$121

Very Good (2 reviews)

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from $121 / night

(4)

1 / 19

Kissimmee Townhouse

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“This was our first time renting a vacation home in Orlando, and it definitely won't be our last! We were pleasantly surprised by the clean and modern vacation home that awaited us after a long day of travel. The amenities were great, and each bedroom...”
- Review left on 01/26/2017

$95

Very Good (4 reviews)

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from $95 / night

(2)

1 / 24

Kissimmee House

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • 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

$115

Excellent (2 reviews)

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from $115 / night

(1)

1 / 8

Kissimmee House

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$85

Excellent (1 reviews)

Inquire

from $85 / night