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Kissimmee Rentals with Pools

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10,632 house rentals in Kissimmee with pools

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. 59 minutes

Match: Swimming pool

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Price per night from

$132

Windsor Hills Luxury pool house/2 miles to Disney

Kissimmee house

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 1 hour 18 minutes

Match: Swimming pool

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Price per night from

$241

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

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

“Great Stay” The house was a better option than hotel rooms. The house was very clean and they had everything necessary for a pleasant stay. They also provided pool towels for the pool or jacuzzi. The jacuzzi was nice and hot and a good option in the evening. Each bedroom had a TV and they had a pool table in the garage. It's a quiet neighborhood. It's not far from Disney or Walmart for groceries.

Responds fast! avg. 3 hours 8 minutes

Match: Swimming pool

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Price per night from

$125

ANY WEEK IN ( JUNE, JULY & AUG ) $1799 (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

$227

Spacious 4-bed lakeside pool villa near Disney

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

“it was a very nice place to stay me and my family loved the stay and would love to stay again.” it is located in a very nice place. because of weather we didn't get to go to some places we wanted but we had a very good time.

Responds fast! avg. 1 hour 33 minutes

Match: Swimming pool

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Price per night from

$138

Gorgeous apartment just minutes to Disney parks, Orlando Florida.

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

$113

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

Kissimmee house

9 bedrooms / 6 bathrooms / sleeps 18

“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. 59 minutes

Match: Swimming pool

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Price per night from

$415

Fantasy Pool Home

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 32 minutes

Match: Swimming pool

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Price per night from

$133

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 6 minutes

Match: Swimming pool

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Price per night from

$98

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. 59 minutes

Match: Swimming pool

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Price per night from

$114

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

Kissimmee villa

7 bedrooms / 6 bathrooms / sleeps 17

Match: Swimming pool

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Price per night from

$355

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. 3 hours 3 minutes

Match: Swimming pool

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Price per night from

$156

From $95/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. 59 minutes

Match: Swimming pool

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Price per night from

$121

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

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 56 minutes

Match: Swimming pool

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Price per night from

$160

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

$182

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 1 minutes

Match: Swimming pool

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Price per night from

$312

The Charming Mickey's Tree House,

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 9

“Mickey Mouse Hut” Wonderful home. Everything you need for a home away from home. Pool was awesome. More than enough pool towels to use. Home was very spacious. Only complaint I had was it was not enough cookware to use to cook meals enough for a large group. Other than that small gesture, I give it 5 stars. Thanks for letting us share another vacation in Florida in your home.

Match: Swimming pool

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Price per night from

$157

⭐ 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

$248

From $100/nt,4br/3ba townhome with hot tub/lake view,Near Disney,Seaworld

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

Match: Swimming pool

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Price per night from

$121

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 43 minutes

Match: Swimming pool

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Price per night from

$103

5br/3ba townhome with hot tub,Near Disney,Seaworld,Convention center

Kissimmee apartment

5 bedrooms / 3 bathrooms / sleeps 10

“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. 59 minutes

Match: Swimming pool

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Price per night from

$125

“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 45 minutes

Match: Swimming pool

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Price per night from

$224

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

$112

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 43 minutes

Match: Swimming pool

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Price per night from

$98

Caribe Cove Resort - 2 BR * Unit Top floor * New Mattress - WiFi/Parking free

Kissimmee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$148

4678CLD. 4 Bed Pool Home In Cumbrian Lakes With Games Room

Kissimmee house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$169

Disney Area 5 Bedroom Home at Veranda Palms

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 28 minutes

Match: Swimming pool

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Price per night from

$231

Beautiful Disney Home-Private Pool, WiFi, Disney/Orlando

Kissimmee house

4 bedrooms / 2 bathrooms / sleeps 8

“Very nice house, nice pool and pool area” Enjoyed our three week stay at this rental. The house was quite nice and the pool and pool areas were terrific. The house is in a very good neighbourhood but is quite a long way from grocery or retail shopping. Some information in the rental instructions would have been helpful. Property manager was helpful when needed.

Responds fast! avg. 1 hour 33 minutes

Match: Swimming pool

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Price per night from

$155

✨Disney Dreams ✨Windsor Hills 3BD/3BA w/FREE Pool Ht & Welcome Package

Kissimmee house

3 bedrooms / 9 bathrooms / sleeps 8

“A Magical Stay” What's not to love about this home! First and foremost Brandie herself is a genuine person who really cares about the people who stay at her home. From the initial contact of a personal phone call, to her follow ups on every little question, to her wishing us a safe trip to a thank you and welcome home at the end, Brandie is truly a great family person! The home itself was as described in other reviews and more. The location to the clubhouse could not have been better. A short walk down the path (100yds maybe) and the kids were relaxing by the lagoon pool! The added security of a gated community provided additional piece of mind even though you are only 5mins from Disney. The staff at the community became like family before we left. Friendly, cheerful, always willing to stop and talk about anything and everything! The home itself is exactly as pictured! Clean and comfortable made for it enjoyable to return home for afternoon breaks from the park. The Disney bedroom was the room of choice for our youngest! The downstairs bedroom provided a nice separation for our oldest to have her space when exhaustion took over:). We have rented homes before when traveling to Disney and Brandie's is at the top of the list! From location, ease of access, amenities, cleanliness, comfort and exceptional (what I will call) customer service and value, you won't find a better place to stay or person to work with then Brandie and her home!!! We will definitely be back again!!! Thanks Brandie :)

Responds fast! avg. 29 minutes

Match: Swimming pool

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Price per night from

$173

Deluxe pool home with games room, 2737

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 21 minutes

Match: Swimming pool

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Price per night from

$172

Amazing Disney Oasis Condo with Sauna and Gym

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 7

Match: Swimming pool

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Price per night from

$126

4BR-2 King-Large Pool/Spa-GamesRm-ROKU-WiFi

Kissimmee house

4 bedrooms / 2 bathrooms / sleeps 8

“Excellent and beautiful home! My family loved it!!” It was absolutely gorgeous and it was beyond even our best expectations. The home was very clean and beautifully decorated and had everything we needed that we couldn't bring from our own home. Our kids didn't even want to leave the home because of the pool would have rather stay here than go anywhere else LOL

Responds fast! avg. 1 hour 33 minutes

Match: Swimming pool

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Price per night from

$155

Fresh poolvilla with free WI-FI and BBQ

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

“Great stay!” When we got to the house it was very clean and felt cozy like you are in you own house. The pool was also great not to mention the kitchen was absolutely good they got everything we needed it to make a good mealfoe my family and save some money.

Responds fast! avg. 3 hours 49 minutes

Match: Swimming pool

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Price per night from

$121

Rocco's Retreat

Kissimmee house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 43 minutes

Match: Swimming pool

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Price per night from

$118

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 59 minutes

Match: Swimming pool

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Price per night from

$115

Sunny Oaks

Kissimmee house

4 bedrooms / 2 bathrooms / sleeps 8

“This has been our second stay in the same house and it's been aw” Sunny Oaks is a beautiful and spacious house. We loved it so much the first time (Aug. 2011) that we rented it again this summer (Aug. 2013). The kids loved the pool and the adults loved the comfort of home. Annie The Bronx, N.Y.

Responds fast! avg. 2 hours 43 minutes

Match: Swimming pool

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Price per night from

$194

Big and Beautiful 9Bed/6Bath Home, Minutes Drive to Disney

Kissimmee house

9 bedrooms / 6 bathrooms / sleeps 22

Responds fast! avg. 1 hour 23 minutes

Match: Swimming pool

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Price per night from

$1,144

Viewing 38 of 10,632
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