Find Hotels with a Pool in Historic Downtown Kissimmee, FL

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Pick from 24 Historic Downtown Kissimmee Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Front of property
Park Royal Orlando
2.5 star property
7.8 out of 10, Good, (1000)
"."
The price is SAR 265
SAR 294 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Park Royal Orlando
Pool
Vivo Flex Living Kissimmee
2.5 star property
6.8 out of 10, (1000)
"Small property. Nice and quiet at night. But after a certain hour no staff are on property. Don’t have any issues. But if I did not sure how long it would take for them to show up"
The price is SAR 270
SAR 299 total
includes taxes & fees
24 Jum. I - 25 Jum. I
Vivo Flex Living Kissimmee
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
Exterior
Days Inn by Wyndham Kissimmee West
2.5 star property
6.0 out of 10, (1001)
"Excellent hotel"
The price is SAR 225
SAR 251 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Days Inn by Wyndham Kissimmee West
Exterior
Super 8 by Wyndham Kissimmee
2.5 star property
5.8 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
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
Front of property
Ambassador Inn
2.0 star property
4.4 out of 10, (713)
"Great place"
The price is SAR 137
SAR 235 total
includes taxes & fees
26 Jum. I - 27 Jum. I
Ambassador Inn
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See all available properties in Historic Downtown Kissimmee
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.

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.
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 Hollywood Studios® 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.

Recent reviews of Historic Downtown Kissimmee hotels
Expedia verified reviews

Rosen Inn International

Rosen Inn International

5/5 Excellent
"Great stay for a few days. Close to everything. Great value, nice staff and clean property. I’ve stayed on their properties many times and this is my favorite location. "
A verified traveler stayed at Rosen Inn International
Posted 17 hours ago
Rosen Inn International