Kailua Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 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

Where to stay in Kailua

Find the best Kailua areas and neighborhoods for the activities you enjoy most. Learn more about Kailua

Find the Best Kailua Vacation Packages

Kailua Hotel Deals

Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

4.5 out of 5
2005 Kalia Rd Honolulu HI
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,123 per night from Aug 8 to Aug 9
SARĀ 1,123
SARĀ 1,577 total
8 Aug - 9 Aug
includes taxes & fees
8.4/10 Very Good! (9,395 reviews)
"1"

Reviewed on 16 July 2026

Hilton Hawaiian Village Waikiki Beach Resort
Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4.5 out of 5
2255 Kalakaua Ave Honolulu HI
Fully refundableReserve now, pay when you stay
The price is SARĀ 2,062 per night from Aug 7 to Aug 8
SARĀ 2,062
SARĀ 2,678 total
7 Aug - 8 Aug
includes taxes & fees
9.2/10 Wonderful! (3,261 reviews)
"very good"

Reviewed on 16 July 2026

Sheraton Waikiki Beach Resort
'Alohilani Resort Waikiki Beach

'Alohilani Resort Waikiki Beach

5 out of 5
2490 Kalakaua Avenue Honolulu HI
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,198 per night from Aug 16 to Aug 17
SARĀ 1,198
SARĀ 1,670 total
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (4,092 reviews)
"Pool"

Reviewed on 16 July 2026

'Alohilani Resort Waikiki Beach
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.

Stay near popular Kailua attractions

Frequently asked questions

How much does a Kailua vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation to Kailua costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Kailua?
April, June and November are great times to search for cheap Kailua vacation packages. Traveling in quieter months means you can generally find reduced prices on accommodations and flights.
How to find the best Kailua package deals?
Finding a cheap Kailua package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Kailua package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Kailua vacation as a package?
You can enjoy significant savings on your Kailua escape by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Kailua?
If you're considering a spur-of-the-moment Kailua vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Kailua?

  1. Choose when to get away: Check your diary and get your bags packed. Your favorite time of year and the activities on offer will also help you decide when to visit Kailua.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to experiences and flights. Your accommodations will probably be the largest expense during your trip to Kailua.
  3. Decide how long to go away for: Now that you know more about Kailua, you can figure out the ideal length of your break. Create a rough plan and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Kailua vacation package.