Find Hotels with a Pool in Historic Downtown Kissimmee, FL

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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, (1004)
"Property was clean, but the door on my room was strange and had to be forced to close all the way. "
The price is SAR 253
SAR 287 total
includes taxes & fees
19 Jan - 20 January 2025
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, (1001)
"Cleanliness of the room. Room space. "
The price is SAR 243
SAR 276 total
includes taxes & fees
1 Jan - 2 January 2025
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, (1003)
"Not bad but needs so upkeep, latch lock on broken, bathroom door wouldn't close"
The price is SAR 282
SAR 320 total
includes taxes & fees
23 Dec - 24 Dec
Days Inn by Wyndham Kissimmee West
Ambassador Inn
Outdoor pool

Ambassador Inn

2.0 star property
4.4 out of 10, (775)
"Okay to stay "
The price is SAR 208
SAR 320 total
includes taxes & fees
23 Dec - 24 Dec
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?
DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Features a children’s pool, an outdoor pool, and 2 restaurants. Avanti International Resort: Hotel, 9-minute walk from Pointe Orlando. Offers a children’s pool, an outdoor pool, and a snack bar/deli. The Grove Resort & Water Park Orlando: Provides 3 outdoor pools, a children’s pool, and free water-park access. Hyatt Regency Orlando International Airport: Features 2 restaurants, an outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Orlando at SeaWorld: Hotel, 8-minute walk from Aquatica. Offers 2 outdoor pools, a children’s 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™, Epcot®, and Disney’s Animal Kingdom® Theme Park 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.