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
Minibar, in-room safe, individually decorated, individually furnished

Park Royal Orlando

2.5 star property
7.8 out of 10, Good, (1006)
"perfect for the price"
The price is SAR 225
SAR 256 total
includes taxes & fees
14 Apr - 15 Apr
Park Royal Orlando
Oak Plantation Resort
2 outdoor pools

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
Indoor pool, 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
Iron/ironing board, free WiFi, bed sheets

Home 1 Suites Extended Stay - Kissimmee

2.5 star property
6.6 out of 10, (1005)
"The property was extremely reasonably priced. Armain was great check-in was super easy at 2 AM. Pool was super clean. Rooms were super clean as well. Everything is blocks away and downtown. Disney is 5 to 10 minutes. This is an extended stay so they do have long-term residence about the property. I had no issues during my stay. My only suggestion would be to have a 24 hour towel exchange through the office. The kids were swimming repeatedly and housekeeping only exchanges towels at 7 AM which...
The price is SAR 239
SAR 272 total
includes taxes & fees
1 May - 2 May
Home 1 Suites Extended Stay - Kissimmee
Super 8 by Wyndham Kissimmee
Exterior

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
Exterior

Days Inn by Wyndham Kissimmee West

2.5 star property
5.8 out of 10, (1001)
"I was charged the amount and did not sleep a single night at the hotel. I was not offered a room at the hotel, the one they had was dirty and full of cockroaches."
Days Inn by Wyndham Kissimmee West
Ambassador Inn
Outdoor pool

Ambassador Inn

2.0 star property
4.6 out of 10, (802)
"I was treated with respect, kindness, and the front desk gave two towels, a washcloth, and a tv remote. The channels on their tv was worth watching. I enjoyed TBS. They were willing to honor online rates for those struggling to book with a debit card online. The bed was extremely comfortable "
The price is SAR 298
SAR 435 total
includes taxes & fees
14 Apr - 15 Apr
Ambassador Inn
Freedom FL Condos of Kissimmee
Condo, 2 Bedrooms | Terrace/patio

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
Exterior

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?
Holiday Inn Resort Orlando Suites - Waterpark by IHG: Hotel located near Old Town. Features a water park, 2 outdoor pools, and 5 restaurants. Hyatt Regency Orlando International Airport: Offers 2 restaurants, an outdoor pool, and complimentary wireless internet access. The Grove Resort & Water Park Orlando: Resort located near Flamingo Crossings Town Center. Provides 6 outdoor pools, a children’s pool, and free water-park access. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Features 2 coffee shops/cafes, 3 outdoor pools, and free self parking. Universal’s Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Offers a lazy river, 2 outdoor pools, 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.