Kailua Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.

Top hotels in Kailua

Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
The price is S$349 per night from 29 Mar to 30 Mar
S$349
29 Mar - 30 Mar
includes taxes & fees
8.8/10 Excellent! (1,300 reviews)
Not clean at all. Very deceiving photos that were not what the property actually looked like.

Reviewed on 13 Mar, 2026

Maui Seaside Hotel
Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
The price is S$456 per night from 7 Apr to 8 Apr
S$456
7 Apr - 8 Apr
includes taxes & fees
9.6/10 Exceptional! (2,546 reviews)
staff was very friendly and accommodating. Property was clean and beautiful. Great location

Reviewed on 13 Mar, 2026

Maui Coast Hotel
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue Kahului HI
Fully refundableReserve now, pay when you stay
The price is S$346 per night from 1 Apr to 2 Apr
S$346
1 Apr - 2 Apr
includes taxes & fees
7.2/10 Good! (1,193 reviews)
The problem with the hotel was the beach. It was dirty and there were garbage everywhere. Also, the staff weren’t necessarily mean, but t OK maybe later

Reviewed on 12 Mar, 2026

Maui Beach Hotel
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.

What to do in Kailua

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.