Search Kissimmee resorts with pools

Our top choices for a great stay

WorldMark Reunion

WorldMark Reunion

4 out of 5
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 10 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (596 reviews)
Opens in a new windowWorldMark Reunion
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
The price is CA $176 per night from Jan 6 to Jan 7
CA $176
CA $275 total
Jan 6 - Jan 7, 2026
includes taxes & fees
Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
8.8/10 Excellent! (3,635 reviews)
Opens in a new windowMargaritaville Resort Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
The price is CA $164 per night from Jan 4 to Jan 5
CA $164
CA $245 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,517 reviews)
Opens in a new windowHoliday Inn Club Vacations at Orange Lake Resort by IHG
FantasyWorld Resort

FantasyWorld Resort

4 out of 5
Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, 2 outdoor pools, and 2 hot tubs. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (1,010 reviews)
Opens in a new windowFantasyWorld Resort
Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl

5 out of 5
The price is CA $343 per night from Dec 21 to Dec 22
CA $343
CA $984 total
Dec 21 - Dec 22
includes taxes & fees
Book a stay at this luxury resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. ...
8.2/10 Very Good! (1,002 reviews)
Opens in a new windowEncore Resort and Water Park at Reunion by Rentyl
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
The price is CA $123 per night from Dec 20 to Dec 21
CA $123
CA $186 total
Dec 20 - Dec 21
includes taxes & fees
Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,382 reviews)
Opens in a new windowWestgate Town Center Resort
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
The price is CA $117 per night from Dec 20 to Dec 21
CA $117
CA $180 total
Dec 20 - Dec 21
includes taxes & fees
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,708 reviews)
Opens in a new windowWestgate Vacation Villas Resort
Hilton Vacation Golf Club Mystic Dunes Resort, Orlando, FL

Hilton Vacation Golf Club Mystic Dunes Resort, Orlando, FL

Stay at this resort in Kissimmee. Enjoy laundry facilities, cable/satellite TV service, and air conditioning. Popular attractions Disney's Animal Kingdom® Theme ...
Opens in a new windowHilton Vacation Golf Club Mystic Dunes Resort, Orlando, FL
Deluxe Golf Resort Jaccuzi Suite near all Orlando attractions

Deluxe Golf Resort Jaccuzi Suite near all Orlando attractions

Stay at this resort in Kissimmee. Enjoy laundry facilities, in-room jetted tubs, and air conditioning. Popular attractions Disney's Animal Kingdom® Theme Park ...
Opens in a new windowDeluxe Golf Resort Jaccuzi Suite near all Orlando attractions
3 NIGHT STAY IN ORLANDO WITH 1 DAY FAMILY PASS TO DISNEY FOR UP TO 4

3 NIGHT STAY IN ORLANDO WITH 1 DAY FAMILY PASS TO DISNEY FOR UP TO 4

Stay at this resort in Kissimmee. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN ...
Opens in a new window3 NIGHT STAY IN ORLANDO WITH 1 DAY FAMILY PASS TO DISNEY FOR UP TO 4
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.