Hotels with a Pool in Historic Downtown Kissimmee, Orlando
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Tomorrow night
Check prices in Historic Downtown Kissimmee for tomorrow night, Dec 16 - Dec 17Featured Historic Downtown Kissimmee Hotels with Pool

Park Royal Orlando
1500 North Thacker Ave Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$66 nightly
The price is $75 total per night
$75 total
Dec 16 - Dec 17
Total with taxes and fees
Guests of Park Royal Orlando have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include an outdoor tennis court, express check-out, and a terrace.
Pool
Pet friendly

Oak Plantation Resort
4090 Enchanted Oaks Circle Kissimmee FL
Guests staying at Oak Plantation Resort enjoy access to 2 outdoor pools, a gym, and free WiFi in public areas. A stay here includes free parking. The front desk has multilingual staff that can help with concierge services, luggage storage, and securing valuables. Additional amenities include an outdoor tennis court, meeting rooms, and a business center.
Pool
Parking included

Ramada by Wyndham Kissimmee Hotel
4018 West Vine Street Kissimmee FL
Ramada by Wyndham Kissimmee Hotel features an indoor pool, an outdoor pool, and a children's pool. You can take advantage of onsite parking for a fee, along with an airport shuttle. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Other amenities at this family-friendly aparthotel include a gym, a hot tub, and conference space.
Pool
Hot Tub

Home 1 Suites Extended Stay - Kissimmee
4156 West Vine Street Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
$60 nightly
The price is $68 total per night
$68 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Home 1 Suites Extended Stay - Kissimmee have access to an outdoor pool, a gym, and free WiFi in public areas. You can put free parking to good use if you drive. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Additional amenities include coffee/tea in a common area, laundry facilities, and a vending machine.
Pool
Pet friendly

Super 8 by Wyndham Kissimmee
1815 W Vine Street Kissimmee FL
At Super 8 by Wyndham Kissimmee, guests have access to an outdoor pool, WiFi in public areas, and a business center. There's free parking if you drive. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include free newspapers and laundry facilities.
Pool
Breakfast included

Days Inn by Wyndham Kissimmee West
4125 W Vine St Kissimmee FL
At Days Inn by Wyndham Kissimmee West, guests have access to an outdoor pool, laundry facilities, and a vending machine. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Other amenities at this golf hotel include a TV in a common area and a picnic area.
Pool
Breakfast included

Ambassador Inn
4107 West Vine Street Kissimmee FL
$45 nightly
The price is $51 total per night
$51 total
Dec 16 - Dec 17
Total with taxes and fees
Guests of Ambassador Inn enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. You can take advantage of free parking if you drive. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include a garden and a vending machine.

Freedom FL Condos of Kissimmee
109 Madiera Beach Blvd Kissimmee FL
Guests of Freedom FL Condos of Kissimmee have access to an outdoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. Additional amenities include an outdoor tennis court, laundry facilities, and a TV in a common area.
Pool
Kitchen
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View all propertiesLowest 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.
Historic Downtown Kissimmee hotels essential information
Accommodation | 54,181 hotels |
|---|---|
Lowest Price | $51 |
Highest Price | $75 |
Popular hotels | Park Royal Orlando, Oak Plantation Resort, Ramada by Wyndham Kissimmee Hotel, Home 1 Suites Extended Stay - Kissimmee, Super 8 by Wyndham Kissimmee, Days Inn by Wyndham Kissimmee West, Ambassador Inn, Freedom FL Condos of Kissimmee, Global Vacation Homes |
Recent Hotels with Pool Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando
5/5 Excellent
"Excellent stay great food an warm cookies…thank you "
A verified traveler stayed at DoubleTree by Hilton at the Entrance to Universal Orlando
Posted 15 hours ago
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