Kissimmee Apartments & Vacation Rentals with Swimming Pool - 2843 Rentals Available.

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2,843 Vacation rentals

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1 / 33

GIANT pool/spa, CLOSE to Disney, GameRm, Free WiFi, Completely private backyard

Kissimmee House

8 bedrooms 8
6 bathrooms
sleeps 22 22
7 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 2 hours 50 minutes

“We loved this home and would definitely book it again when traveling with a large group. Whether you have a toddler or a teenager in your group, this house has everything you?ll need. The pool is awesome and the house was very clean. The location is...”

- Review left on 10/13/2019

$251.00

Excellent (11 reviews)

from $251.00 / night

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1 / 51

Disney 5 Star Vacations / The Osprey Villa

Kissimmee Villa

5 bedrooms 5
4 bathrooms
sleeps 10 10
5 nights min

Swimming pool
Child friendly
Air conditioning

“This home was perfect for us just as it has been for previous stays. We keep coming back to this wonderful home because it accommodates us so well. Thank you again for letting us call this house home for another week...”

- Review left on 02/18/2019

$144.00

Excellent (74 reviews)

from $144.00 / night

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1 / 28

CW4- Just 1 mile to Disney, Nice Townhouse in a Gated Community

Kissimmee Townhouse

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

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

$102.00

Excellent (23 reviews)

from $102.00 / night

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1 / 27

CW14- 3 Bdrm TownHome 1 mile from Disney

Kissimmee House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Nearest beach 60 mi
Swimming pool
Child friendly

$102.00

Average (8 reviews)

from $102.00 / night

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1 / 29

Disney World... Minutes Away! Luxury 6 BR/4 BA

Kissimmee Villa

6 bedrooms 6
4 bathrooms
sleeps 14 14
2 nights min

Swimming pool
Ask about children
Air conditioning

Responds fast! Avg. 29 minutes

“This home was beautiful and clean better than what we thought. The home was conveniently located near shopping centers...”

- Review left on 12/29/2019

$224.00

Very Good (5 reviews)

from $224.00 / night

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1 / 23

Summer and fall specials now call for more details or dates

Kissimmee Apartment

3 bedrooms 3
2 bathrooms
sleeps 8 8
3 nights min

Nearest beach 72 mi
Swimming pool
Child friendly

Responds fast! Avg. 2 hours 22 minutes

$91.00

Excellent (3 reviews)

from $91.00 / night

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1 / 27

CW2- 1 mile from Disney, nice town home in Gated Community

Kissimmee Townhouse

3 bedrooms 3
3 bathrooms
sleeps 8 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

$102.00

Very Good (53 reviews)

from $102.00 / night

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1 / 43

Stunning Lake View House 2mls to Disney,games room

Kissimmee House

4 bedrooms 4
3 bathrooms
sleeps 8 8
5 nights min

Beach/lakeside relaxation
Swimming pool
Child friendly

Responds fast! Avg. 3 hours 28 minutes

“Great location. Near Disney and shops. The owner were very nice ? called to see if everything is o.k, and agreed to a late departure. The view of the lake is wonderful and the pool is great. The kids rooms upstairs was the one thing I liked less....”

- Review left on 10/17/2018

$172.00

Excellent (43 reviews)

from $172.00 / night

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1 / 42

Amazing 8 Bedrooms 7 bath Orlando Villa with private pool | 6 miles from Disney

Kissimmee House

8 bedrooms 8
7 bathrooms
sleeps 18 18
min stay varies

Nearest beach 56 mi
Swimming pool
Child friendly

Responds fast! Avg. 1 hour 36 minutes

Travelers’ Choice award

“This vacation home is absolutely beautiful! It looks identical to the pictures on the website. We stayed at the Reunion Emperor in March 2017 for a total of 8 nights. Our group consisted of 6 adults and 7 children - three families all under one...”

- Review left on 01/20/2018

$263.00

Excellent (17 reviews)

from $263.00 / night

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1 / 50

NEW 5 BR/Ensuite home w/ private pool in Luxury Resort w/ Lazy River from $213nt

Kissimmee House

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 34 minutes

$233.00

Excellent (5 reviews)

from $233.00 / night

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1 / 40

4 Bed/3 bath Condo with only 2 miles to Disney

Kissimmee Apartment

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 41 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

$92.00

Very Good (14 reviews)

from $92.00 / night

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1 / 45

KENNEDY#1 PRIVATE POOL AND SPA! AHHHH!! EAGLE POINTE IN KISSIMMEE

Kissimmee House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Travelers’ Choice award

“All around great stay. Bob and Diane were extremely helpful. Would highly recommend them for your vacation needs...”

- Review left on 07/29/2018

$104.00

Very Good (9 reviews)

from $104.00 / night

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1 / 48

Themed rooms, lots of space no crowds!

Kissimmee Villa

6 bedrooms 6
4 bathrooms
sleeps 14 14
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 59 minutes

Travelers’ Choice award

“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

$172.00

Excellent (22 reviews)

from $172.00 / night

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1 / 50

Check Into a Beautiful Resort w/ Deluxe Room+Premium Living Space+Nearby Disney

Kissimmee Villa

7 bedrooms 7
5 bathrooms
sleeps 16 16
3 nights min

Nearest beach 97 mi
Swimming pool
Child friendly

“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

$115.00

Excellent (4 reviews)

from $115.00 / night

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1 / 41

Windsor Hills 3 Bedroom Condo, Less Than 2 Miles to Disney

Kissimmee Apartment

3 bedrooms 3
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Car not necessary

Responds fast! Avg. 1 hour 16 minutes

$114.00

Very Good (4 reviews)

from $114.00 / night

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1 / 47

⭐Beautiful Lake View 7BR Villa - Near Orlando Parks and Attractions⭐

Kissimmee Villa

7 bedrooms 7
5 bathrooms
sleeps 14 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

$188.00

Excellent (1 reviews)

from $188.00 / night

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1 / 38

4BD/3BA,RENOVATED,EXECUTIVE VILLA WITH SPA,MUST SEE,10 MIN FROM DISNEY

Kissimmee Villa

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 13 minutes

$109.00

Excellent (17 reviews)

from $109.00 / night

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1 / 23

Luxury 5 Star 4 Bedroom Waterfront Villa

Kissimmee Villa

4 bedrooms 4
3 bathrooms
sleeps 8 8
2 nights min

Beach/lakeside relaxation
Swimming pool
Child friendly

Responds fast! Avg. 1 hour 20 minutes

“From the time we viewed this beautiful home on the website, we knew this was the place we wanted to celebrate our 2nd. Anniversary here. This place is decorated with a touch of sophistication and elegance yet it made you feel at home once you walked...”

- Review left on 10/07/2015

$109.00

Average (4 reviews)

from $109.00 / night

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1 / 94

7 Beds/7 Baths,SOUTH FACING POOL WITH WATER VIEW,ALL NEW FURNITURE,10 MIN. DISNEY

Kissimmee Villa

7 bedrooms 7
7 bathrooms
sleeps 16 16
min stay varies

Beach/lakeside relaxation
Nearest beach 113 mi
Swimming pool

Responds fast! Avg. 1 hour 13 minutes

$172.00

from $172.00 / night

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1 / 25

⭐Great Deal - 3 Bedrooms Town Home - Near Disney⭐

Kissimmee Townhouse

3 bedrooms 3
3 bathrooms
sleeps 7 7
3 nights min

Nearest beach 90 mi
Swimming pool
Child friendly

“Will recommended to friends when they are planning to go Orlando in July/August.Closed to Disney world, shopping centres, etc...”

- Review left on 04/18/2016

$70.00

Excellent (12 reviews)

from $70.00 / night

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1 / 26

7 Bedroom 5 Bath Lakeview House near Disney

Kissimmee House

7 bedrooms 7
6 bathrooms
sleeps 15 15
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

$184.00

Very Good (13 reviews)

from $184.00 / night

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1 / 19

Exclusive Orlando Vacation Home

Kissimmee House

4 bedrooms 4
3 bathrooms
sleeps 10 10
2 nights min

Swimming pool
Child friendly
Air conditioning

“We had a last minute vacation opportunity and Sheryl was so accommodating and excellent and we loved her place! We had 5 kids and 2 adults and there was tons of space to relax and have private space. The pool was amazing!! It was the perfect temp and...”

- Review left on 07/07/2018

$137.00

Very Good (35 reviews)

from $137.00 / night

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1 / 25

Tropical Seasons-2 master suites-Pool & Spa- game room-6 mi to Disney-South Pool

Kissimmee House

4 bedrooms 4
3 bathrooms
sleeps 10 10
5 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 59 minutes

Travelers’ Choice award

“We were quite happy with our stay. The house was clean and comfortable. The pool however was not cleaned prior to us coming so we were unable to use it out first week. They came and cleaned it after calling about it. The area was also quiet and...”

- Review left on 08/02/2018

$121.00

Very Good (7 reviews)

from $121.00 / night

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1 / 64

DISNEY ORLANDO LAKE 4 BED LUXURY POOL VILLA

Kissimmee Villa

4 bedrooms 4
2 bathrooms
sleeps 8 8
5 nights min

Beach/lakeside relaxation
Swimming pool
Child friendly

Responds fast! Avg. 3 hours 23 minutes

Travelers’ Choice award

“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

$138.00

Excellent (27 reviews)

from $138.00 / night

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1 / 56

⭐Beautiful 8 BR - Near to Disney / Universal / SeaWorld - Great Deal!⭐

Kissimmee Villa

8 bedrooms 8
6 bathrooms
sleeps 18 18
min stay varies

Nearest beach 90 mi
Swimming pool
Child friendly

“We had the best vacation ever and this property was everything a family my size needed and more.. I will recommend this to anyone that I come in contact with because it was so comfortable,convenient,spacious,nicely decorated and it was not far from...”

- Review left on 04/07/2016

$229.00

Average (2 reviews)

from $229.00 / night

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1 / 118

Regal Oaks Resort - 3BR/2BH, 3 miles to Disney,Water slides,WiFi,Behind Old Town

Kissimmee House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Car not necessary

Responds fast! Avg. 1 hour 59 minutes

$75.00

Excellent (4 reviews)

from $75.00 / night

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1 / 18

Spring Hill - 6 Bedroom Luxury Pool Home at Windsor Hills

Kissimmee House

6 bedrooms 6
4 bathrooms
sleeps 14 14
5 nights min

Swimming pool
Child friendly
Air conditioning

$264.00

from $264.00 / night

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1 / 2

5 bed 3 bath Disney Villa, Pool, Spa, Netflix

Kissimmee Villa

5 bedrooms 5
3 bathrooms
sleeps 11 11
min stay varies

Nearest beach 115 mi
Swimming pool
Child friendly

$125.00

Very Good (4 reviews)

from $125.00 / night

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1 / 40

Lake Berkley- Lakefront Home w/ Pool, HotTub,10 miles to Disney

Kissimmee Villa

6 bedrooms 6
4 bathrooms
sleeps 12 12
7 nights min

Beach/lakeside relaxation
Nearest beach 120 mi
Swimming pool

Responds fast! Avg. 27 minutes

Travelers’ Choice award

“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

$229.00

Excellent (10 reviews)

from $229.00 / night

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1 / 59

Regal Oaks Resort - Beautiful 4 BR/4BT,1900Sq.3 Mi to Disney,New Pool/Slide,WiFi

Kissimmee Villa

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Car not necessary

Responds fast! Avg. 1 hour 20 minutes

$81.00

Very Good (15 reviews)

from $81.00 / night

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1 / 41

Debbie's Florida Retreat a Luxury Vacation Home

Kissimmee House

4 bedrooms 4
2 bathrooms
sleeps 8 8
3 nights min

Nearest beach 125 mi
Swimming pool
Child friendly

Responds fast! Avg. 1 hour 38 minutes

Travelers’ Choice award

“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

$144.00

Excellent (58 reviews)

from $144.00 / night

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1 / 30

Luxurious Disney Home at Venetian Bay Villages

Kissimmee Townhouse

3 bedrooms 3
2 bathrooms
sleeps 8 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

$75.00

Very Good (55 reviews)

from $75.00 / night

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1 / 102

2 miles to Disney, Beautiful Home that Sleeps 8 (2 families)

Kissimmee Townhouse

3 bedrooms 3
3 bathrooms
sleeps 8 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

$86.00

Excellent (89 reviews)

from $86.00 / night

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1 / 19

Private Secluded Pool - 8 Miles to Disney

Kissimmee Villa

4 bedrooms 4
2 bathrooms
sleeps 8 8
3 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 2 hours 3 minutes

Travelers’ Choice award

“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

$115.00

Very Good (12 reviews)

from $115.00 / night

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1 / 47

Affordable luxury! 3 bdrm pet friendly pool home 4 mi from Disney.

Kissimmee House

3 bedrooms 3
2 bathrooms
sleeps 8 8
3 nights min

Swimming pool
Child friendly
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

$114.00

Excellent (6 reviews)

from $114.00 / night

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1 / 75

Superb 4 Bedroom Home, just 3 minutes from Disney

Kissimmee House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Nearest beach 72 mi
Swimming pool
Child friendly

Responds fast! Avg. 30 minutes

Travelers’ Choice award

“This house was the perfect setting for our Disney vacation! Each young person in our group of 5 enjoyed having the privacy of having their own bedroom and bathroom. The house was extremely clean, well-equipped and convenient to all! Although we...”

- Review left on 07/13/2018

$155.00

Excellent (50 reviews)

from $155.00 / night

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1 / 28

4 Bedroom 2 Bath with Pool & Spa

Kissimmee House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Travelers’ Choice award

“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

$104.00

Excellent (15 reviews)

from $104.00 / night

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1 / 41

New Upgraded Luxury Villa w/ Frozen & Star Wars Rooms at Encore!

Kissimmee House

6 bedrooms 6
7 bathrooms
sleeps 16 16
min stay varies

Swimming pool
Child friendly
Air conditioning

$344.00

Excellent (3 reviews)

from $344.00 / night

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1 / 49

♥ 5 Min To Disney - Game Room, Salt Water Pool W/ Free Pool Heat, BBQ, Baby Gear

Kissimmee House

6 bedrooms 6
4 bathrooms
sleeps 16 16
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

$264.00

Excellent (2 reviews)

from $264.00 / night

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1 / 19

The Kennedy #5

Kissimmee House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Beach/lakeside relaxation
Swimming pool
Child friendly

“This vacation was a winner and Bob and Dianne provided us with a fantastic and welcoming vacation home rental. It was so peaceful and relaxing. The home was very clean and well maintained. I would strongly recommend this property to anyone visiting...”

- Review left on 05/13/2018

$98.00

Excellent (6 reviews)

from $98.00 / night

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