Find Hotels with a Pool in Historic Downtown Kissimmee, FL

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Check availability on Historic Downtown Kissimmee Hotels with a Pool

Compare Historic Downtown Kissimmee Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Park Royal Orlando
Outdoor pool

Park Royal Orlando

2.5 star property
7.8 out of 10, Good, (1002)
"We stayed in room C216 and it was renovated and very clean. My only suggestion would be to upgrade the beds. We were literally laying on the springs "
The price is SAR 244
SAR 277 total
includes taxes & fees
24 Feb - 25 Feb
Park Royal Orlando
Oak Plantation Resort
Pool

Oak Plantation Resort

2.5 star property
6.6 out of 10, (433)
"Quiet location, clean rooms, property is old but well maintained"
Oak Plantation Resort
Ramada by Wyndham Kissimmee Hotel
Outdoor pool

Ramada by Wyndham Kissimmee Hotel

2.5 star property
5.6 out of 10, (999)
"Do not stay here terrible service we moved rooms three times first they provided a room with lots of mold on the sheets ceiling and smelled bad. At that point I thought I would sleep in my van rather then sleeping there. They moved us to another room and air conditioner didn’t work then they moved us to another room and card system didn’t work leak in ceiling as well. After 5 days they only cleaned room once. Also did not provide toilet paper or clean towels. Do not stay here!,,"
Ramada by Wyndham Kissimmee Hotel
Home 1 Suites Extended Stay - Kissimmee
Pool

Home 1 Suites Extended Stay - Kissimmee

2.5 star property
6.8 out of 10, (1003)
"Nice and clean rooms, love the amenities "
The price is SAR 243
SAR 276 total
includes taxes & fees
9 Feb - 10 Feb
Home 1 Suites Extended Stay - Kissimmee
Super 8 by Wyndham Kissimmee
Pool

Super 8 by Wyndham Kissimmee

2.5 star property
6.0 out of 10, (1000)
"One of our rooms smelled like people had been smoking in it and both rooms had roaches in them. The A/C didn’t work the best"
Super 8 by Wyndham Kissimmee
Days Inn by Wyndham Kissimmee West
Pool

Days Inn by Wyndham Kissimmee West

2.5 star property
5.8 out of 10, (1001)
"Rooms are very old and outdated. Beds were all stained. Had to change rooms because tv didn’t work. Just didn’t feel comfortable in the area it was located. They said they offered breakfast but no one told us where to go for it and we didn’t see any signs. "
The price is SAR 281
SAR 319 total
includes taxes & fees
9 Feb - 10 Feb
Days Inn by Wyndham Kissimmee West
Ambassador Inn
Outdoor pool

Ambassador Inn

2.0 star property
4.6 out of 10, (789)
"Good"
The price is SAR 298
SAR 421 total
includes taxes & fees
8 Feb - 9 Feb
Ambassador Inn
Freedom FL Condos of Kissimmee
Outdoor pool

Freedom FL Condos of Kissimmee

3.5 star property
6.8 out of 10, (23)
"I love everything. "
Freedom FL Condos of Kissimmee
Global Vacation Homes
Outdoor pool

Global Vacation Homes

3.5 star property
5.2 out of 10, (5)
"The carpet was stained. The pots and pans and dishes were not clean . There were no wash clothes and not enough towels for 8. But home was nice. The microwave needs to be replaced.. handle broke and a crack in the door. They need to do better up keep on the small things.. "
Global Vacation Homes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

What's it like visiting Historic Downtown Kissimmee?
If relaxing by the pool is your idea of a great vacation, you may want to consider Historic Downtown Kissimmee, which has 10 places to stay with pools. While you’re here, you can explore sights such as Disney Springs® Area and Disney Springs®, and then unwind poolside at one of the accommodations in Historic Downtown Kissimmee that guests like for their pools.
What are some accommodations with pools in Historic Downtown Kissimmee?
The Grove Resort & Water Park Orlando: Features 3 outdoor pools, a children’s pool, and free water-park access. Rosen Inn Lake Buena Vista: Hotel located near Disney Springs™. Offers 2 outdoor pools, a children’s pool, and a snack bar/deli. Hyatt Regency Orlando International Airport: Provides 2 restaurants, an outdoor pool, and complimentary wireless internet access. Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel: Hotel located near Disney Springs™. Features a water park, 2 outdoor pools, and 5 restaurants. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Offers a children’s pool, an outdoor pool, and 2 restaurants.
How many pool hotels will I find in Historic Downtown Kissimmee?
Expedia has 10 hotels in Historic Downtown Kissimmee for your poolside break.
What is there to see and do in Historic Downtown Kissimmee?
Explore places like Disney Springs™, Disney’s Animal Kingdom® Theme Park, and Universal Orlando Resort while you’re in the area. Spend some time experiencing the great outdoors at Kissimmee Lakefront Park and Lake Tohopekaliga. Visitors have positive things to say about the major shopping area in Historic Downtown Kissimmee.
When is the best time to book a hotel with a pool in Historic Downtown Kissimmee?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Kissimmee in the driest months of December, February, or November when the average rainfall is 2 inches. Lodging that has a pool indoors 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.