Find Hotels with a Pool in Historic Downtown Kissimmee, FL

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Check availability on Historic Downtown Kissimmee Hotels with a Pool

Our top choices for Historic Downtown Kissimmee hotels with a pool

Outdoor pool, pool umbrellas, sun loungers
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1365)
"The staff was really friendly and the property was nice and cozy "
United States
curtis
The price is NT$3,400
NT$3,825 total
includes taxes & fees
Dec 16 - Dec 17
Hyatt House Orlando International Drive
Outdoor pool, open 8:00 AM to 9:00 PM, cabanas (surcharge)
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
International Drive District
8.8 out of 10, Excellent, (693)
"Clean rooms, friendly staff, delicious breakfast "
United States
Katherin
The price is NT$2,360
NT$2,655 total
includes taxes & fees
Jan 5 - 2026/1/6
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Reception
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1983)
"Great stay! Beautiful hotel with amazing rooms and an awesome location."
United States
Andrew
The price is NT$1,517
NT$2,961 total
includes taxes & fees
Dec 16 - Dec 17
Kompose Boutique Resort at Theme Parks
Front of property
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
Kissimmee
8.2 out of 10, Very Good, (5160)
"Beautiful place to stay."
United States
Mohammad
The price is NT$685
NT$1,839 total
includes taxes & fees
Dec 16 - Dec 17
Palazzo Lakeside Hotel
Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4365)
"Great resort "
United States
Camille
The price is NT$3,469
NT$3,902 total
includes taxes & fees
Dec 18 - Dec 19
Rosen Shingle Creek
Outdoor pool
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
Kissimmee
8.8 out of 10, Excellent, (3305)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is NT$1,895
NT$2,151 total
includes taxes & fees
Dec 16 - Dec 17
Seasons Florida Resort
Outdoor pool, pool umbrellas, sun loungers
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
Orlando
8.8 out of 10, Excellent, (1910)
"Great stay"
United States
Gerard
The price is NT$2,433
NT$2,737 total
includes taxes & fees
Dec 18 - Dec 19
Aloft Orlando Lake Buena Vista
Terrace/patio
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1239)
"Excellent hotel. Beautiful, accommodating, comfortable. "
United States
Solimar
The price is NT$3,811
NT$4,326 total
includes taxes & fees
Dec 22 - Dec 23
Embassy Suites by Hilton Orlando Lake Buena Vista South
2 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas, sun loungers
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
Kissimmee
8.4 out of 10, Very Good, (1047)
"Excellent Location, the hotel is very clean. Friendly staff, delicious breakfast. Overall a wonderful experience "
United States
Nabesy
The price is NT$1,962
NT$2,846 total
includes taxes & fees
Dec 18 - Dec 19
Holiday Inn Resort Kissimmee by the Parks by IHG
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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Top Historic Downtown Kissimmee Hotel Reviews

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent
"The property is a little rundown, but the service is good, the price is great and the cookies are yummy. I stayed there twice and will definitely stay there again."
Max 1-night trip
Posted 13 hours ago
DoubleTree by Hilton Hotel Orlando at SeaWorld

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Frequently asked questions

What are some accommodations with pools in Historic Downtown Kissimmee?
Universal's Cabana Bay Beach Resort: Hotel, 5-minute walk from Universal Orlando Resort. Features a lazy river, 2 outdoor pools, and 2 restaurants. Rosen Inn at Pointe Orlando: Hotel, 2-minute walk from Pointe Orlando. Offers 2 coffee shops/cafes, 3 outdoor pools, and complimentary wireless internet access. DoubleTree by Hilton at the Entrance to Universal Orlando: Hotel, 2-minute walk from Universal Orlando Resort. Provides a children's pool, an outdoor pool, and 2 restaurants. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Features 6 outdoor pools, a children's pool, and 3 restaurants. Hyatt Regency Orlando: Hotel, 2-minute walk from Orange County Convention Center. Offers a children's pool, an outdoor pool, and 3 restaurants.
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.