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Kissimmee Rentals with Pools

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5,203 house rentals in Kissimmee with pools

Fantasy Pool Home

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$138

5Br/3Ba townhome with lake View,Close Disney,Seaworld,Convention Center

Kissimmee townhouse

5 bedrooms / 3 bathrooms / sleeps 10

“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. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$146

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.

Responds fast! avg. 3 hours 11 minutes

Match: Swimming pool

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Price per night from

$123

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

$125

Spacious 4-bed lakeside pool villa near Disney

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

“Great Location” We stayed from Saturday to Saturday. Overall the house was good. Pros: Clean, spacious, close to Disney Parks, close to stores, very quite place, easy access, comfortable furnitures, Cons: master bedroom was hot, internet service went down mostly at night time like it has a timer at night, and odd times during day time only for few minutes, the pool only the first day when we arrived pool was with cloudy water and water very hot all the time, we think the heater was on. Cable TV, we had two afternoons that we had no signal. The house has two blenders both not working. No raw meat knife, we had to buy our own for cooking. We wanted to use the garage to place our car, it has many objects we could not use it.

Responds fast! avg. 3 hours 50 minutes

Match: Swimming pool

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Price per night from

$146

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. 2 hours 39 minutes

Match: Swimming pool

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Price per night from

$175

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. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$126

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. 1 hour 52 minutes

Match: Swimming pool

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Price per night from

$109

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. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$134

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

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

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. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$146

From $110/nt,4br/3ba townhome with lake view,Near Disney,Seaworld

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$134

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. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$344

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

$149

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. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$435

✨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. 37 minutes

Match: Swimming pool

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Price per night from

$195

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.

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. 1 hour 2 minutes

Match: Swimming pool

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Price per night from

$205

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

Kissimmee house

8 bedrooms / 6 bathrooms / sleeps 18

“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.

Responds fast! avg. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$344

5 Bed Luxury Vacation Home in Kissimmee FL

Kissimmee house

5 bedrooms / 5 bathrooms / sleeps 10

“Great home & location.” Beautiful and private, with plenty of space. My family enjoyed our stay here. Loved the location and spaciousness of rooms as well as pool & backyard.

Match: Swimming pool

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Price per night from

$207

⭐ 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

$265

M8631 Pondview Luxury 8 Bedroom Villa, New Remodel

Kissimmee house

8 bedrooms / 5 bathrooms / sleeps 20

Match: Swimming pool

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Price per night from

$217

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

$125

Close Disney,Seaworld,Convention center, 5BR towwnhome with hot tub/lake view

Kissimmee house

5 bedrooms / 3 bathrooms / sleeps 10

“Good price for family of 10” With 5 bedrooms, fits 10 comfortably. Owner is very helpful and location is 20mins from the parks. Walmart and restaurants are very close.

Responds fast! avg. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$146

“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 51 minutes

Match: Swimming pool

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Price per night from

$258

Luxury Lakeside House with private solar heated pool & spa

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 12

“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 9 minutes

Match: Swimming pool

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Price per night from

$184

1 mile from Margaritaville/Island H2O and 3 miles from Disney World

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

“Close to Disney” This house was perfect for our family's first visit to Disney. It's very close to the parks, so getting to the parks right as they opened every day was no problem at all!

Responds fast! avg. 3 hours 25 minutes

Match: Swimming pool

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Price per night from

$132

Sleeps up to 10 in this fully equipped home- Calabria in Kissimmee

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 10

“Great” Great and awesome we really enjoyed it. The front room TV volume was going in and out sometimes but overall it was great. The rooms was nice and comfortable and we loved both master bedrooms. The game room is something we need at our house and the pool are with the screen in porch was amazing. Thanks again we appreciate it

Responds fast! avg. 2 hours 37 minutes

Match: Swimming pool

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Price per night from

$217

Beautiful home with private pool and themed bedroom near Disney

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 20 minutes

Match: Swimming pool

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Price per night from

$148

1 Bed Resort Suite #6, Only 2 Miles from

Kissimmee apartment

1 bedroom / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$102

✦Rest in This Phenomenal Family Villa✦Cozy Baby Friendly Rooms = Restful Days✦

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$117

Match: Swimming pool

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Price per night from

$86

The Retreat - Explore Disney & Florida in style

Kissimmee villa

4 bedrooms / 4 bathrooms / sleeps 10

“Wonderful Vacation Spot” The Retreat is a great place to stay with your family. The accommodations were well equipped, clean and a it's a great location. Brian is responsive and very nice to work with. I could not say anything bad about The Retreat.

Match: Swimming pool

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Price per night from

$172

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. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$137

Luxury 4 Bed 3 Bath Villa with own pool. Games room. Gated Resort near Disney.

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

“Beautiful Home! Close to all Attractions” Booked stay for 8 nights, We were not there for Disney but very close if you have young kids. Beds were comfortable, Great Kitchen, House was immaculate when we arrived, the table was even set. All the amenities of Home.Close to Super Walmart, Publix and Restaurants. The only thing that could of been a little better was the pool, it needed to be vacuumed and the pool person never showed up for the 9 days that we were there, and all the management company said was they weren't sure what day they would be there. But other than that it was great! Very quiet gated community! Was very safe! I highly recommend staying at this home.

Responds fast! avg. 2 hours 25 minutes

Match: Swimming pool

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Price per night from

$161

Disney Vacation Rental, Private Townhouse in gated community

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$126

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

Kissimmee house

9 bedrooms / 6 bathrooms / sleeps 22

Match: Swimming pool

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Price per night from

$1,144

Viewing 38 of 5,203
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