Find Hotels with a Pool in Historic Downtown Kissimmee, FL

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Check availability on Historic Downtown Kissimmee Hotels with a Pool

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, (33)
"We really enjoyed our stay! Close to riverfront park where we loved the sunsets and walking with our dog. We also enjoyed the convenience to golf courses and we took a guided fishing trip on Lake Toho. The home is well stocked with everything you need. Loved the pool and privacy. Pool table is a nice touch as well. Great communication with the owner."
United States
Teri K.
The price is AED 529
AED 1,614 total
includes taxes & fees
19 Nov - 20 Nov
Beautiful home near Disney Private PoolBBQ Downtown
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, (2640)
"Very nice , clean and friendly place to stay with friends and family "
United States
Ariana
The price is AED 155
AED 301 total
includes taxes & fees
1 Dec - 2 Dec
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
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, (600)
"Awesome hotel. And the great price is an added bonus!"
United States
Khristo
The price is AED 278
AED 313 total
includes taxes & fees
7 Dec - 8 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, (1787)
"Everything about the hotel was excellent, from location to amenities. "
United States
Sheilla Maria
The price is AED 224
AED 400 total
includes taxes & fees
18 Nov - 19 Nov
Kompose Boutique Resort at Theme Parks
Outdoor pool
Seasons Florida Resort

Seasons Florida Resort

2.0 star property
Kissimmee
8.8 out of 10, Excellent, (3242)
"Great place!"
United States
Andrea
The price is AED 194
AED 220 total
includes taxes & fees
25 Nov - 26 Nov
Seasons Florida Resort
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

3.5 star property
Kissimmee
8.4 out of 10, Very Good, (953)
"My family and I really enjoyed our stay. "
United States
Melesia
The price is AED 213
AED 315 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Resort Kissimmee by the Parks by IHG
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, (1864)
"Great stay"
United States
Ramprasad
The price is AED 257
AED 289 total
includes taxes & fees
1 Dec - 2 Dec
Aloft Orlando Lake Buena Vista
Outdoor pool, pool umbrellas, sun loungers
DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport

4.0 star property
Airport North
8.8 out of 10, Excellent, (2063)
"Excellent hotel for relaxing "
United States
Lind M
The price is AED 358
AED 403 total
includes taxes & fees
24 Nov - 25 Nov
DoubleTree by Hilton Orlando Airport
Outdoor pool
Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL

3.0 star property
Airport North
7.8 out of 10, Good, (4217)
"We had a great stay. The room, breakfast, and staff were great. "
United States
Jeidyn
The price is AED 255
AED 287 total
includes taxes & fees
9 Dec - 10 Dec
Country Inn & Suites by Radisson, Orlando Airport, FL
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers
Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL

3.5 star property
International Drive District
9.0 out of 10, Wonderful, (3555)
"Perfect hotel for a quick stay, clean not too noisy."
United States
Rachel
The price is AED 291
AED 327 total
includes taxes & fees
23 Nov - 24 Nov
Tru By Hilton Orlando Convention Center Area, FL
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 at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Good "
Gustavo 1-night trip
Posted 8 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

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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. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando: Hotel located near Disney Springs™. Offers 6 outdoor pools, a children's pool, and 3 restaurants. 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. Ramada by Wyndham Suites Orlando Airport: Features a snack bar/deli, an outdoor pool, and daily. 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.
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.