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Kissimmee Rentals with Pools

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18,166 house rentals in Kissimmee with pools

Kissimmee Townhouse 4 bedrooms

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

“Great Place” This vacation home is absolutely beautiful and convenient to everything. Still here and having a great time.

Responds fast! avg. 2 hours 58 minutes

Match: Swimming pool

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Price per night from

$142

FIVE STAR 3BR Pool Home, ROKU Apps, HBO, GamesRm, WiFi, BBQ,Clean,Disney/Orlando

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 7

“Great Home, Safe & quiet neighborhood” I will be "Renting this Vacation Home Again" Home was clean. My RATING for this Home and Customer servive is *** A+*****. Beutiful Home. Thank you again Tonya.

Responds fast! avg. 1 hour 37 minutes

Match: Swimming pool

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Price per night from

$132

New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld,Convention Center

Kissimmee townhouse

5 bedrooms / 3 bathrooms / sleeps 12

“Ok” Overall it was fine..checkout was at 11 and at 10 cleaners knocked on door and then preceded to sit in driveway waiting for us to leave. There was no dish soap or soap in bathrooms which would have been nice.

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$117

Windsor Hills Luxury pool house/2 miles to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 1 hour 53 minutes

Match: Swimming pool

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Price per night from

$233

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

“Beautiful Home, It was so relaxing and comfortable!!” Our family had a wonderful time on our Vacation. The location was very convenient. The pool and hot tub was great. The house was amazing, and my children loved it, I like the entrance to the pool and the alarm system that secured our safety. I also like the pool tables, and how close the area is to Disney. The experience was wonderful!!!!!

Match: Swimming pool

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Price per night from

$128

WE ARE BACK (JULY-SEPTEMBER) $1350 (includes TAXES & Final Cleaning)

Kissimmee house

4 bedrooms / 5 bathrooms / sleeps 10

“Awesome Stay!” Can't say enough great things about this property. It was everything as described and pictured. The location was perfect being only about 20 minutes from the Disney parks. The pool, which is beautiful, was a welcome addition after spending a day at the park. Everything about the home is fantastic. The quiet setting was also a treat to come home to after spending busy days at the parks. Our host, Mr. Randenella was always prompt when asking questions. He definitely takes pride in his home as is evident in the way it is taken care of. Our whole family was sad to leave and can't wait to return. This home made our dream vacation very memorable. We will definitely recommend this property to others and hope to return again soon.

Match: Swimming pool

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Price per night from

$162

Pat and Ron's Holiday Home, Relaxing Retreat

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

“Good” I was a little disappointed this time. I have been going there since 2015. In the past when I had minor problems with the home, the response was quick. This time I called on Saturday to ask about no input message on the tv screen, I was told me they would come on Sunday to check it. They come on Sunday and knocked at 10:30 but we were sleep and did not hear them, so I called again and someone came over in about 1 and 30 minutes. I pointed out that the main bathroom in the hall had a problem with the bathroom and needed to get fixed. He looked at it and said he needed a piece for the door and he would fix it on Monday. I told him people were getting locked up inside. Well I left on 12/18/18 and no one ever came to fix the lock on the door. The clean in the kitchen needed some attention with the over. I did not get a chance to show anyone as no one came back to fix the door. The oven has some spilled grease on the bottom and needed to be cleaned before I got there. These are minor issues with me, that I lived with and had a good time, I would come again. The management should realize that certain things the guests are not responsible for even though it may seem small to them, but it is not small for the renter. I do not have then same cable company that is used where I was, so I did not complain about it when it went off and on and in and out half the day, it is not my fault nor was it the fault of Pat and Ron so I did not complain about it.

Match: Swimming pool

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Price per night from

$115

Spacious 4-bed lakeside pool villa near Disney

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 10

“Peaceful location with stunning views” We had a wonderful holiday in this lovely villa. It is spacious and well appointed everything was beautifully clean. The estate is quiet and peaceful considering how close it is to the 192 and all it has to offer this is a pleasant surprise. The villa has a wonderful view from the pool area, watching the local wildlife with a cuppa in the early morning is a real treat . The pool area is also very private and not overlooked from either side. The only thing that could be improved is the air conditioning system could be left at a constant temperature as it could be hot and uncomfortable at night and ceiling fans were a bit noisy to leave on.

Responds fast! avg. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$119

Close2theMagic 3br/3ba Townhouse Windsor Hills

Kissimmee house

3 bedrooms / 3 bathrooms / sleeps 7

“Vacation comfort at its Best!” This was a family vacation to bring my 5 yr old granddaughter to Disney for her first time. It was spectacular! The condo was so close to Disney that we could be there in a few minutes. The heated splash pool was so awesome and having three bathrooms was very nice. My grandaughter especially loved her Mickey room & bathroom, she is still talking about it now. The condo is very spacious so it felt like we were in a big house which gave everyone space. The Windsor Hills pool & playground were absolutely beautiful. On Saturday we went to a pool party there with a DJ and fun and games... couldn't really ask for more...its paradise...would definately recommend anyone to stay there, it was fabulous... can't wait to go back...

Responds fast! avg. 2 hours 14 minutes

Match: Swimming pool

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Price per night from

$141

Furnished apartment - weekly & monthly Orlando rental.

Kissimmee hotel apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Place to stay” I stayed at the Island Club for a period of 3 months and was very happy with my stay. It was quiet, and comfortable. I liked the layout of my condo which was on one floor. My family of 5 had plenty of room to enjoy. I also liked how there was a patio in back. It made it feel more like a home. We stayed on the top floor where there was vaulted ceilings and lots of windows in the front room. This made it feel more spacious and rich. The amenities were additionally nice as well. There were 2 different pools and jacuzzis, tennis court, clubhouse and work out room to enjoy. I also liked how you could park right up against your condo building. The location was very convieinent as well. It is close to all major attractions. 15 minutes from Disney - 25 from Universal and close to shopping, and restaurants. I would stay here again in a heart beat!

Match: Swimming pool

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Price per night from

$92

New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney

Kissimmee house

9 bedrooms / 6 bathrooms / sleeps 20

“Great time!” House was a perfect fit for my family. We had a great time and plan on making this a yearly trip. Central to everything, but far enough away you didn’t feel trapped. Would highly recommend it!

Responds fast! avg. 1 hour 32 minutes

Match: Swimming pool

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Price per night from

$310

Fantasy Pool Home

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Match: Swimming pool

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Price per night from

$134

Furnished 4 Bedroom Villa for Rent

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$236

2636TW- Veranda Palms

Kissimmee house

6 bedrooms / 5 bathrooms / sleeps 13

Responds fast! avg. 15 minutes

Match: Swimming pool

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Price per night from

$158

Luxurious 3 Bedroom Townhome-1.5 miles from Disney

Kissimmee villa

3 bedrooms / 3 bathrooms / sleeps 7

“Great Experience” The villa did not disappoint and was a great place for my family and I to stay during our world wind visit to Disney. I would recommend this place to anyone who is going to Orlando with a large group :-)

Responds fast! avg. 2 hours 17 minutes

Match: Swimming pool

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Price per night from

$112

1.5 M to Disney,From $70/nt,3BR 1600 sqft Townhome

Kissimmee apartment

3 bedrooms / 3 bathrooms / sleeps 8

“Spacious family friendly condo close to Disney.” Perfect location to visit Disney. Very spacious with a full kitchen . A great family friendly condo.

Responds fast! avg. 1 hour 32 minutes

Match: Swimming pool

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Price per night from

$88

Kissimmee Windsor at Westside's "The Second Star to the Right" vacation home

Kissimmee villa

7 bedrooms / 6 bathrooms / sleeps 17

Responds fast! avg. 3 hours 8 minutes

Match: Swimming pool

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Price per night from

$332

Luxury Lakeside House with private solar heated pool & spa

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 13

“Wonderful vacation home” I rented this house for 6 days for our family’s Disney vacation. The house was wonderful. Great location, very clean. Everything we needed was provided. Would definitely book again.

Responds fast! avg. 2 hours 51 minutes

Match: Swimming pool

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Price per night from

$112

From $80/nt,Close to Disney,Seaworld,Convention Center,4br Townhome with Hot Tub

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

“Great Family Friendly Home” We had a blast. It felt safe and secure. It was clean and spacious. I have a large family of 9 and everyone had plenty of space. Quiet but friendly neighbors. Amenities were awesome. Hot tub was so relaxing. We had a great time.

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$106

NEW! 4/3 Private Town Home at Storey Lake Resort-Near Disney Theme Parks

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 9 minutes

Match: Swimming pool

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Price per night from

$115

NEW LISTING! 3-Bedroom Resort Villa

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 10

“Beautiful Resort” The unit was absolutely spacious. Chris was very helpful in booking the unit. He told me that the unit number was assigned by the resort and it would be look identical to the pictures. The unit that was assigned to us was exactly as shown in the pictures. We were located on the third floor and it had a balcony with a great view of the pond. Plenty of kitchen space and bathrooms. The master suite that i stayed in had a jacuzzi and own bathroom. I only wish I had more time to check out the resorts amenities, but since I traveled from VA my family and I went to all the major Orlando attractions. But even with that said you can't go wrong staying at Star Island resort. I would love to go back.

Match: Swimming pool

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Price per night from

$179

Terra Verde 5 Bedroom with Conservation View

Kissimmee villa

5 bedrooms / 3 bathrooms / sleeps 10

“Very nice” The home was just as promised. It was clean and well kept. The location was a straight shot to disney. We didn't have to go on the toll road. Terra verde was great also. I liked the idea of a safe and secure place to stay in a home away from home. The tiki bar was a nice plus to the swimming pool and sauna area. A shuttle service to disney would have made it a little better. Parking at disney is now $17 per day. We had two cars to park. The only two negatives were the fact that the dishwasher was inop. and the dining room chairs were showing signs of wear. Thank You Crystal for all of your help and renting us a great place to vacation.

Responds fast! avg. 2 hours 14 minutes

Match: Swimming pool

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Price per night from

$247

Spectacular 8 bedroom home close to Disney

Kissimmee hotel apartment

8 bedrooms / 5 bathrooms / sleeps 17

Match: Swimming pool

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Price per night from

$253

New Opening 8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

8 bedrooms / 6 bathrooms / sleeps 18

“Family vacation” This by far was the best we went to. There is something for everyone to do down to the kids, the house was beautiful.

Responds fast! avg. 1 hour 32 minutes

Match: Swimming pool

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Price per night from

$266

The Charming Mickey's Tree House,

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 9

“Awesome vacation!!” My husband and I took our 3 year old daughter and had a wonderful time. The house had everything we needed and more. We felt right at home from the time we got there until the time we went home. The pool and hot tub were perfect and with the fence around the pool, we did not have to worry about our little girl. The location of the house is perfect and we could not have ask for better weather. Geoff was very helpful and gave us several suggestions of things to do while we were there. We will be planning another vacation in 2013 and definitely plan to stay in this villa again.

Match: Swimming pool

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Price per night from

$115

2605GR - The Villas at Seven Dwarfs

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 55 minutes

Match: Swimming pool

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Price per night from

$125

⭐ Near Disney and Other Theme Parks - Comfortable 6 BR ⭐

Kissimmee villa

6 bedrooms / 5 bathrooms / sleeps 14

Match: Swimming pool

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Price per night from

$148

From $80/nt,4br/3ba townhome with hot tub/lake view,Near Disney,Seaworld

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$106

Safari Lodge

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 8

“Cozy clean stay” Great access to everything. Very clean cozy house, The staff was very friendly and quickly addressed our concerns when there was an issue with the pool alarm. my friends and I had a great stay here!

Responds fast! avg. 2 hours 14 minutes

Match: Swimming pool

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Price per night from

$95

From $90/nt,5br/3ba townhome with hot tub,Near Disney,Seaworld,Convention center

Kissimmee apartment

5 bedrooms / 3 bathrooms / sleeps 12

“Vacation rental” The overall experience was nice. The hot was only hot for one day and wouldn't get hot again there after. The cookware needs to be updated but overall we had a great time. I wouldn't definitely rent this rental again.

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$117

Stunning 6 Bed Pool Home Close to Disney Parks.

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 12

“Wonderful!” First of all I would like to thank Julie, the owner, for all the excellent help and advice she gave me before and during our stay. Belles Palace is wonderful, it is more than home from home! It's just perfect in every way. The photos are great but the villa is even more stunning when you are there. We all loved the fabulous big comfortable beds, they were fit for a palace. There was nothing that hadn't been thought about. If you book this villa, you will have the most fabulous time and won't want to go home!

Responds fast! avg. 3 hours 31 minutes

Match: Swimming pool

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Price per night from

$247

“Wonderful, Relaxing, Well Worth it!” We loved this home it was larger than expected. The pool area was outstanding, we had warm sunshine all day and pool was very warm. We also saw alligators & birds almost everyday! Close to all amenities, we walked neighborhood daily and it was very safe, neighbors would wave hello. Robert was very helpful and truthful about everything he described about his home , we will definitely rent again!!

Responds fast! avg. 3 hours 11 minutes

Match: Swimming pool

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Price per night from

$160

Our Disney Lodge - Vacation in the Florida Sun

Kissimmee villa

6 bedrooms / 5 bathrooms / sleeps 14

Match: Swimming pool

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Price per night from

$216

Caitlins Disney Condo - Spacious and convenient

Kissimmee apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Clean, quiet, comfortable, and roomy!” We have a large family, with 5 kids. We brought my mother with us on vacation, giving us a whopping 8 people to accommodate, for a week and this condo gave us plenty of space and beds for everyone to sleep comfortably! The gated community is great! Clean and quiet with plenty of parking.

Match: Swimming pool

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Price per night from

$117

6 bedrooms luxury home, best location

Kissimmee house

6 bedrooms / 5 bathrooms / sleeps 16

Match: Swimming pool

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Price per night from

$233

100 Aker Woods

Kissimmee house

4 bedrooms / 2 bathrooms / sleeps 8

“AMAZING!!!” This house was Wonderful! Exactly as described! Loyalty USA was GREAT to work with!!! Very pleased all around!!!!

Responds fast! avg. 2 hours 14 minutes

Match: Swimming pool

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Price per night from

$113

3 Bedroom Vacation Home in Kissimmee Pet-Friendly

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 6

“Vacation 2017” The house is really beautiful, clean and well maintained. We had a wonderful time and really felt at home. The owner Philip was very friendly and helpful. Thanks to Al for setting up the internet for us. Hoping to come back again next year.

Match: Swimming pool

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Price per night from

$92

Pool Paradise

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 8

“relaxing” Love the house, 2nd time we have stayed there. The only problem was the 1st night the pool heat had not been turned on so we couldn't swim that night. (disappointed) In close driving distance to all parks. Plenty of room.

Responds fast! avg. 2 hours 14 minutes

Match: Swimming pool

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Price per night from

$98

Viewing 38 of 18,166
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