Find Hotels with a Pool in Kissimmee, FL from CA $52

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May 13 - May 14
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May 14 - May 15
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May 17 - May 19
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May 24 - May 26

Top Kissimmee Hotels with a Pool

Lobby
Hilton Vacation Club Polynesian Isles Kissimmee
3.0 star property
9.8 out of 10, Exceptional, (1601)
"Great customer service, very clean, kid friendly. Highly recommended, and would definitely stay here again! "
The price is CA $110
CA $156 total
includes taxes & fees
May 27 - May 28
Hilton Vacation Club Polynesian Isles Kissimmee
Outdoor pool, sun loungers
Parkway International Resort
3.0 star property
9.2 out of 10, Wonderful, (1557)
"Enjoyed our stay for summit cheer competition. Front desk staff is super friendly & helpful. The place is clean, quiet, and comfortable. Everything you can think, they prepared in the kitchen. Close to everything. Highly recommended!!!"
The price is CA $141
CA $183 total
includes taxes & fees
May 19 - May 20
Parkway International Resort
4 outdoor pools, cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando
3.5 star property
8.8 out of 10, Excellent, (3103)
"We arrived in Orlando at 11am. We took a chance and called to see if a room was ready. We were told our room was ready and we could come on over and check in. Check in was quick and easy. Our 2 bedroom suite was clean and nice. We loved the full kitchen. We went and bought groceries instead of eating out every day. The balcony is huge and screened in. The property is beautiful and always clean. The pools have plenty of chairs and umbrellas. We liked the text message communication with the front...
The price is CA $119
CA $182 total
includes taxes & fees
May 20 - May 21
Hilton Vacation Club Mystic Dunes Orlando
2 outdoor pools, a heated pool, cabanas (surcharge), pool umbrellas
FantasyWorld Resort
4.0 star property
8.8 out of 10, Excellent, (1332)
"We really liked the water park, the kids never got bored. The villa was gorgeous. Definitely will go back."
FantasyWorld Resort
Front of property
Gaylord Palms Resort & Convention Center
4.0 star property
8.8 out of 10, Excellent, (1119)
"Nice stay"
The price is CA $395
CA $504 total
includes taxes & fees
May 19 - May 20
Gaylord Palms Resort & Convention Center
Exterior
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
4.0 star property
8.4 out of 10, Very good, (1364)
"Highly recommend this property over other options in the area. Close to theme parks and shopping. When we first checked in we were assigned a very old unit (in Cypress Circle). The carpets were old and the bathrooms were dated - not like the pictures we saw online. We went back to the Registration Desk and spoke with Daniel who switched us to a newly renovated condo located in a building in the Tennis Villa Circle. Daniel was so helpful and kind - and made our stay much more pleasant. "
The price is CA $176
CA $239 total
includes taxes & fees
May 14 - May 15
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
Outdoor pool
Staybridge Suites Orlando Royale Parc Suites, an IHG Hotel
3.0 star property
8.2 out of 10, Very good, (1078)
"The 2 bedroom suite was very spacious. Was just missing some kitchen items."
The price is CA $141
CA $188 total
includes taxes & fees
May 19 - May 20
Staybridge Suites Orlando Royale Parc Suites, an IHG Hotel
2 outdoor pools, sun loungers
Delta Hotels by Marriott Orlando Celebration
3.5 star property
8.0 out of 10, Very good, (852)
"The location was very close to all the parks and very convenient. I was extremely disappointed with how our initial encounter was with Ramon and Dave when we first arrived. Expedia customer service representative was beyond excellent. Maria from Delta, I want to say thank you from the bottom of my heart!"
The price is CA $127
CA $183 total
includes taxes & fees
May 14 - May 15
Delta Hotels by Marriott Orlando Celebration
Lobby sitting area
Magic Moment Resort and Kids Club
4.0 star property
8.0 out of 10, Very good, (813)
"Nice for family budget friendly good breakfast "
The price is CA $67
CA $117 total
includes taxes & fees
Jun 2 - Jun 3
Magic Moment Resort and Kids Club
Exterior
Park Royal Orlando
2.5 star property
7.8 out of 10, Good, (1004)
"Loved it "
The price is CA $83
CA $94 total
includes taxes & fees
Jun 3 - Jun 4
Park Royal Orlando
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Frequently asked questions

What's it like visiting Kissimmee?
If taking it easy by the pool is your idea of a great vacation, you may want to consider family-friendly Kissimmee, which has 469 places to stay with pools. During your trip, you can explore sights such as Disney Springs™ and Epcot®, and then relax poolside at one of the accommodations in Kissimmee that guests like for their pools.
What are some accommodations with pools in Kissimmee?
Margaritaville Resort Orlando: Resort located near Disney’s Animal Kingdom® Theme Park. Features 3 restaurants, 3 outdoor pools, and a full-service spa. Margaritaville Cottages Orlando by VStays: Hotel located near Disney’s Animal Kingdom® Theme Park. Offers 4 restaurants, 2 outdoor pools, and 2 bars. Hilton Vacation Club Mystic Dunes Orlando: Hotel located near ESPN Wide World of Sports. Provides 4 outdoor pools, a children’s pool, and 2 bars. Westgate Vacation Villas Resort: Resort located near Walt Disney World® Resort. Features 14 outdoor pools, a children’s pool, and a water park. Red Lion Hotel Orlando Lake Buena Vista South: Hotel located near Old Town. Offers a lazy river, an outdoor pool, and 2 restaurants.
How many pool hotels will I be able to find in Kissimmee?
Expedia’s 469 hotels in Kissimmee give you a great choice for your poolside getaway.
What is there to see and do in Kissimmee?
Explore places like Walt Disney World® Resort, Disney’s Animal Kingdom® Theme Park, and Old Town while you’re in Kissimmee. Make a point to visit attractions like Give Kids the World Village and Fun Spot America. Kissimmee appeals to visitors with its array of dining options, lively festivals, and fun-filled attractions.
When is the best time to book a hotel with a pool in Kissimmee?
You may want to consider a place to stay that offers an outdoor swimming pool if you’ll be visiting Kissimmee in the driest months of December, February, or November when the average rainfall is 2 inches. Lodging with an indoor pool may be the way to go if you are visiting during the rainiest months of August, July, and September when the average rainfall is 8 inches.
What's the best way to travel around Kissimmee?
Knowing the transportation options in Kissimmee can help you enjoy the area beyond your hotel pool. Nearby metro stations include Tupperware Station and Poinciana Station. To venture out into the surrounding area, ride aboard one of the trains from Kissimmee Station.