Find Hotels with a Pool in Historic Downtown Kissimmee, FL

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Check availability on Historic Downtown Kissimmee Hotels with a Pool

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Historic Downtown Kissimmee Hotels with a Pool

Outdoor pool
Beautiful home near Disney Private PoolBBQ Downtown

Beautiful home near Disney Private PoolBBQ Downtown

Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (35)
"House was very clean and we enjoyed the space very much. "
United States
Amy M.
The price is SAR 600
SAR 1,728 total
includes taxes & fees
8 Dec - 9 Dec
Beautiful home near Disney Private PoolBBQ Downtown
Outdoor pool, pool umbrellas, sun loungers
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1334)
"Room, Breakfast, location AAAA+ "
United States
Ahmed Gabriel
The price is SAR 436
SAR 490 total
includes taxes & fees
16 Dec - 17 Dec
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

3.0 star property
International Drive District
8.8 out of 10, Excellent, (651)
"Hospitable staff and nice rooms."
United States
Iryna
The price is SAR 267
SAR 300 total
includes taxes & fees
14 Dec - 15 Dec
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Outdoor pool, pool umbrellas, sun loungers
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (1909)
"Beautiful resort with very friendly staff. "
United States
kristie
The price is SAR 229
SAR 409 total
includes taxes & fees
18 Dec - 19 Dec
Kompose Boutique Resort at Theme Parks
Royal Room, 2 Queen Beds, Pool View | Pool | Outdoor pool, a heated pool, open 9 AM to 9:00 PM, free cabanas
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

3.0 star property
Kissimmee
8.4 out of 10, Very Good, (2680)
"Very nice , clean and friendly place to stay with friends and family "
United States
Ariana
The price is SAR 112
SAR 255 total
includes taxes & fees
9 Dec - 10 Dec
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
Outdoor pool
Seasons Florida Resort

Seasons Florida Resort

2.0 star property
Kissimmee
8.8 out of 10, Excellent, (3274)
"Great room and service. "
United States
Derrick
The price is SAR 497
SAR 564 total
includes taxes & fees
2 Jan - 3 January 2026
Seasons Florida Resort
Outdoor pool, pool umbrellas, sun loungers
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

3.0 star property
Orlando
8.8 out of 10, Excellent, (1897)
"Great rooms, staff, and property!"
United States
Cindy
The price is SAR 278
SAR 312 total
includes taxes & fees
14 Dec - 15 Dec
Aloft Orlando Lake Buena Vista
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)
Rosen Shingle Creek

Rosen Shingle Creek

4.5 star property
Orlando
9.4 out of 10, Exceptional, (4320)
"Great resort "
United States
Camille
The price is SAR 371
SAR 418 total
includes taxes & fees
14 Dec - 15 Dec
Rosen Shingle Creek
Outdoor pool, pool umbrellas, sun loungers
La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North

3.0 star property
Airport North
7.4 out of 10, Good, (782)
"Near the beach , very nice people at the reception. "
United States
Leonie
The price is SAR 297
SAR 334 total
includes taxes & fees
8 Dec - 9 Dec
La Quinta Inn & Suites by Wyndham Orlando Airport North
Outdoor pool
Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village

3.0 star property
Airport North
9.4 out of 10, Exceptional, (2435)
"Great location to airport and food choices. "
United States
Aliza
The price is SAR 372
SAR 419 total
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn & Suites Orlando Airport @ Gateway Village
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

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"Great location! Accessibly to all of the parks, shopping, restaurants local culture. Highly recommended…we will be back soon!"
Rosalyn 5-night trip
Posted 1 day ago
Lake Buena Vista Resort Village & Spa

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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.