Search 105,200+ Vacation Rentals

Kissimmee Apartments & Vacation Rentals with Swimming Pool - 3115 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

3,115 Vacation rentals

Filters applied: Swimming pool

(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

$125.00

Excellent (57 reviews)

Book

from $125.00 / night

1 / 86

Kissimmee Villa

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

Responds fast! Avg. 1 hour 19 minutes

$150.00

Book

from $150.00 / night

(15)

Certificate of Excellence

1 / 38

Kissimmee Villa

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

Responds fast! Avg. 3 hours 5 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

$199.00

Excellent (15 reviews)

Book

from $199.00 / 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

$79.00

Excellent (7 reviews)

Book

from $79.00 / night

(1)

1 / 52

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

$164.00

Excellent (1 reviews)

Book

from $164.00 / 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)

Book

from $100.00 / night

(1)

1 / 47

Kissimmee Apartment

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

Responds fast! Avg. 2 hours 32 minutes

$100.00

Excellent (1 reviews)

Book

from $100.00 / night

(33)

Certificate of Excellence

1 / 12

Kissimmee Villa

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

Responds fast! Avg. 2 hours 4 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 (33 reviews)

Book

from $100.00 / 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)

Book

from $299.00 / night

(2)

1 / 94

Kissimmee Villa

  • 7
  • 18
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“This is a big house! Three families would have no problems here and plently of space not to be under each others feet. Close to Disney and main route to all the normal popular attractions. House was clean and tidy, kitchen had everything should you...”
- Review left on 04/20/2015

$164.00

Excellent (2 reviews)

Book

from $164.00 / night

(1)

1 / 49

Kissimmee House

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

$259.00

Excellent (1 reviews)

Book

from $259.00 / 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)

Book

from $89.00 / night

(17)

1 / 38

Kissimmee Villa

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

Responds fast! Avg. 1 hour 19 minutes

$95.00

Excellent (17 reviews)

Book

from $95.00 / night

(5)

1 / 84

Kissimmee House

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

Responds fast! Avg. 2 hours 16 minutes

$70.00

Excellent (5 reviews)

Book

from $70.00 / night

(40)

Certificate of Excellence

1 / 75

Kissimmee House

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

Responds fast! Avg. 1 hour 32 minutes

Certificate of Excellence

$140.00

Excellent (40 reviews)

Book

from $140.00 / night

1 / 21

Kissimmee Townhouse

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

Responds fast! Avg. 1 hour 52 minutes

$39.00

Book

from $39.00 / night

1 / 45

Kissimmee Villa

  • 10
  • 20
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$526.00

Book

from $526.00 / night

(42)

1 / 36

Kissimmee House

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

$150.00

Excellent (42 reviews)

Book

from $150.00 / 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)

Book

from $165.00 / 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)

Book

from $195.00 / night

(28)

1 / 19

Kissimmee House

  • 4
  • 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 27 minutes

“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

$119.00

Very Good (28 reviews)

Book

from $119.00 / 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)

Book

from $89.00 / night

(2)

1 / 18

Kissimmee House

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

Responds fast! Avg. 3 hours 44 minutes

$199.00

Excellent (2 reviews)

Book

from $199.00 / night

1 / 35

Kissimmee House

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

Responds fast! Avg. 23 minutes

$95.00

Book

from $95.00 / 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)

Book

from $143.00 / night

(3)

1 / 118

Kissimmee House

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

Responds fast! Avg. 2 hours 16 minutes

$70.00

Very Good (3 reviews)

Book

from $70.00 / night

(14)

1 / 59

Kissimmee Villa

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

Responds fast! Avg. 2 hours 16 minutes

$70.00

Very Good (14 reviews)

Book

from $70.00 / 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)

Book

from $62.00 / night

(51)

1 / 41

Kissimmee House

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

Responds fast! Avg. 1 hour 3 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

$115.00

Excellent (51 reviews)

Book

from $115.00 / 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)

Book

from $69.00 / night

(12)

1 / 28

Kissimmee Villa

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

Responds fast! Avg. 2 hours 35 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)

Book

from $209.00 / night

1 / 25

Kissimmee Villa

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

$169.00

Book

from $169.00 / night

(54)

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

$65.00

Very Good (54 reviews)

Book

from $65.00 / night

(1)

1 / 33

Kissimmee Villa

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

Responds fast! Avg. 2 hours 32 minutes

$100.00

Excellent (1 reviews)

Book

from $100.00 / 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)

Book

from $80.00 / 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)

Book

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)

Book

from $69.00 / night

(8)

1 / 29

Kissimmee Villa

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

Responds fast! Avg. 54 minutes

“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

$160.00

Excellent (8 reviews)

Book

from $160.00 / night

(7)

1 / 26

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“Overall, our experience was good. Just be aware that you may get switched to a different unit than the pictured one that you select. We were switched twice before our arrival: once to a completely different community and again to a nearby unit. This...”
- Review left on 08/19/2017

$85.00

Very Good (7 reviews)

Book

from $85.00 / night

(9)

1 / 33

Kissimmee House

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

Responds fast! Avg. 53 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

$189.00

Excellent (9 reviews)

Book

from $189.00 / night