Kailua Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Kailua Vacation

Book a Kailua vacation package and get ready to experience the best of this lively city. Think about staying in the neighborhood of Haiku, which is good for views, walking and nature. During your trip to Kailua, give yourself plenty of time for sightseeing. A popular place to begin is Twin Falls. Whoever you're escaping with and whether your budget is big or small, your ultimate Kailua vacation is just a few clicks away with Expedia.

Top Kailua Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kihei Kai Nani
Maui Beach Vacation Club
Maui Banyan Vacation Club
Palms at Wailea Maui
The Residences at Kamaole Sands Resort

Ready to book your vacation to Kailua?

 

Choose your dates

Kailua Hotel Deals

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 CA $279 per night from Jul 5 to Jul 6
CA $279
CA $373 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (1,470 reviews)
"The is an excellent little resort by the airport. It is right on the beach and has an adorable coffee shop/bakery a quick walk down the street. The attached restaurant was really good a well. The staff was very friendly and the amenities on the grounds-pool, yard games, etc were great. It was the ..."

Reviewed on Jun 23, 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 CA $330 per night from Jul 20 to Jul 21
CA $330
CA $457 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (2,639 reviews)
"Staff was lovely! Food amazing at the cafe and pool bar. Room was very clean. Have stayed here twice and both times were amazing!"

Reviewed on Jun 23, 2026

Maui Coast Hotel
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

4 out of 5
575 S Kihei Road Kihei HI
The price is CA $585 per night from Jun 29 to Jun 30
CA $585
CA $744 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (329 reviews)
"very nice facility"

Reviewed on Jun 22, 2026

Hilton Grand Vacations Club Maui Bay Villas
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.