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Kissimmee 2-bedroom Apartments, Vacation Rentals & More - 3844 Rentals Available.

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3,844 Vacation rentals

Filters applied: 2+ Bedrooms

(10)

1 / 21

Kissimmee Townhouse

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

Responds fast! Avg. 3 hours 8 minutes

$100.00

Excellent (10 reviews)

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from $100.00 / night

(20)

1 / 16

Kissimmee Villa

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The property itself was very nice with a few small problems. We had to purchase an HDMI cable in order to view the TV in the family room which we left on the set. The lamp in the family room was damaged by a previous renter and inoperable. Upstairs...”
- Review left on 04/15/2018

$143.00

Excellent (20 reviews)

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from $143.00 / night

(53)

1 / 27

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • 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

$89.00

Very Good (53 reviews)

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from $89.00 / night

(4)

1 / 29

Kissimmee Villa

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

Responds fast! Avg. 57 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

$195.00

Very Good (4 reviews)

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from $195.00 / night

(22)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“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

$89.00

Excellent (22 reviews)

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from $89.00 / night

(7)

1 / 51

Kissimmee Townhouse

  • 4
  • 8
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“What an amazing home, comfort and just a home away from home. Kids thoroughly enjoyed the splash pool and took advantage of it numerous times and thought they had died and gone to heaven in this very comfortable home. We have recommended it to many...”
- Review left on 05/03/2012

$69.00

Excellent (7 reviews)

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from $69.00 / night

(6)

1 / 37

Kissimmee Villa

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

Responds fast! Avg. 49 minutes

$299.00

Excellent (6 reviews)

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from $299.00 / night

(3)

1 / 22

Kissimmee Villa

  • 5
  • 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 10 minutes

“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

(57)

1 / 51

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great big house Excellent location for parks Very reasonable Owner gave great directions for when you show up Also pool really came in handy”
- Review left on 06/28/2018

$126.00

Excellent (57 reviews)

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from $126.00 / 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

(10)

1 / 19

Kissimmee Villa

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

Responds fast! Avg. 54 minutes

“Accommodation was perfect. We wanted a relaxing weekend getaway and this home more than exceeded our expectations. We will definitely book this house again...”
- Review left on 09/19/2017

$100.00

Very Good (10 reviews)

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from $100.00 / night

(1)

1 / 33

Kissimmee Villa

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

Responds fast! Avg. 2 hours 32 minutes

$99.00

Excellent (1 reviews)

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from $99.00 / night

(3)

1 / 23

Kissimmee Apartment

  • 3
  • 8
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

$69.00

Excellent (3 reviews)

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from $69.00 / night

(13)

Certificate of Excellence

1 / 12

Kissimmee House

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

Certificate of Excellence

“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

$80.00

Excellent (13 reviews)

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from $80.00 / night

(1)

1 / 27

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

$69.00

Excellent (1 reviews)

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from $69.00 / night

(16)

1 / 17

Kissimmee Apartment

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

Responds fast! Avg. 1 hour 9 minutes

$89.00

Excellent (16 reviews)

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from $89.00 / night

1 / 35

Kissimmee House

  • 4
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 28 minutes

$95.00

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from $95.00 / night

(6)

1 / 22

Kissimmee Villa

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

Responds fast! Avg. 1 hour 12 minutes

$195.00

Excellent (6 reviews)

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from $195.00 / night

(51)

1 / 41

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 18 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

$119.00

Excellent (51 reviews)

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from $119.00 / night

(29)

1 / 105

Kissimmee Villa

  • 7
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Went to Disney for six days, adults and kids had a blast. The house was in fine condition and the amenities were great. Plenty of room for the 12 of us...”
- Review left on 05/31/2018

$179.00

Very Good (29 reviews)

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from $179.00 / night

(5)

Certificate of Excellence

1 / 27

Kissimmee Villa

  • 5
  • 10
  • 3 nights min
  • Nearest beach 77 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 29 minutes

Certificate of Excellence

“The house was wonderful! The home was is in great condition, very clean. Had all the amenities to keep the family busy. The pool was fantastic, with lots of toys for the kiddos, as well as separate pool towels. Lots of extras such as blankets, towels...”
- Review left on 04/03/2014

$121.00

Very Good (5 reviews)

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from $121.00 / night

(2)

1 / 18

Kissimmee House

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

$199.00

Excellent (2 reviews)

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from $199.00 / night

(5)

1 / 39

Kissimmee House

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

Responds fast! Avg. 3 hours 0 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

$115.00

Excellent (5 reviews)

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from $115.00 / night

(8)

Certificate of Excellence

1 / 33

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

$70.00

Excellent (8 reviews)

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from $70.00 / night

(6)

1 / 19

Kissimmee Townhouse

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
“Oakwater was very clean. The pictures were true. My family and I stayed for two weeks. We would definitely stay here again in the future...”
- Review left on 08/28/2017

$89.00

Very Good (6 reviews)

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from $89.00 / night

1 / 9

Kissimmee Villa

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

$240.00

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from $240.00 / night

(9)

1 / 33

Kissimmee House

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

Responds fast! Avg. 50 minutes

“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

$190.00

Excellent (9 reviews)

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from $190.00 / night

(14)

1 / 33

Kissimmee Apartment

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

Responds fast! Avg. 3 hours 51 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

$80.00

Very Good (14 reviews)

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from $80.00 / night

(5)

1 / 84

Kissimmee House

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

Responds fast! Avg. 2 hours 17 minutes

$70.00

Excellent (5 reviews)

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from $70.00 / night

(69)

1 / 23

Kissimmee Townhouse

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

Responds fast! Avg. 2 hours 28 minutes

“My Wife and I and Her Brother and his wife ( we are all in our mid sixties) stayed in this rental for the month of February. When we arrived everything was set up well for us from clean linens to the dining room table all set for a meal. The...”
- Review left on 03/08/2017

$55.00

Very Good (69 reviews)

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from $55.00 / night

(12)

1 / 28

Kissimmee Villa

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

Responds fast! Avg. 2 hours 23 minutes

“My wife and I took all four of our children, their spouses and all three of our grandchildren on vacation and stayed in this house which was perfect. We could not have been happier with the home...”
- Review left on 03/14/2015

$209.00

Very Good (12 reviews)

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from $209.00 / night

(4)

1 / 31

Kissimmee House

  • 4
  • 10
  • min stay varies
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“This home is both beautiful and clean with plenty to do. It was so nice to relax while the children played pool and air hockey. We all loved the pool and hot tub! It was also nice having two bedrooms with bathrooms in them! The other two bedrooms...”
- Review left on 09/03/2015

$110.00

Very Good (4 reviews)

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from $110.00 / night

(9)

1 / 16

Kissimmee Condo

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

Responds fast! Avg. 2 hours 28 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

$62.00

Excellent (9 reviews)

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from $62.00 / night

(34)

Certificate of Excellence

1 / 12

Kissimmee Villa

  • 4
  • 8
  • 4 nights min
  • Nearest beach 105 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 23 minutes

Certificate of Excellence

“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

$100.00

Very Good (34 reviews)

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from $100.00 / night

(9)

1 / 98

Kissimmee Villa

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

Responds fast! Avg. 3 hours 11 minutes

$160.00

Very Good (9 reviews)

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from $160.00 / night

(4)

1 / 29

Kissimmee Condo

  • 3
  • 6
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“We loved the location close to the Disney parks (By the way, the Disney park is not 2 miles away, but rather the highway TO the park is 2 miles away). We loved the decor and the general accommodations. The house was well supplied with every...”
- Review left on 04/14/2016

$59.00

Excellent (4 reviews)

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from $59.00 / night

(12)

1 / 26

Kissimmee House

  • 7
  • 16
  • 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

$150.00

Very Good (12 reviews)

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from $150.00 / night

(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

$199.00

Very Good (8 reviews)

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from $199.00 / night

(55)

1 / 30

Kissimmee Townhouse

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

$59.00

Very Good (55 reviews)

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from $59.00 / night

(9)

1 / 12

Kissimmee House

  • 2
  • 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 2 hours 22 minutes

“I stayed for 5months at this house and it was great. Had everything needed to cook, fenced in backyard for my dog, neighbors were great and I was only 10 minutes from give kids the world where I volunteered. Lots of places to eat and close to all...”
- Review left on 04/11/2016

$85.00

Excellent (9 reviews)

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from $85.00 / night