Kailua Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Lahaina Shores Beach Resort By Castle
CA $1,605
per person
Nov 11 - Nov 17
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
No reviews
Everything we needed for our stay in Maui! Spectacular on the beach location and views. The unit had all the big and little things we needed. Look forward to returning.
Reviewed on Aug 31, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
CA $6,986
per person
Nov 6 - Nov 13
found 20 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,006 reviews)
Everything was excellent! The room, the amenities and staff! I had one meal—breakfast, and that too was perfection!
Reviewed on Sep 1, 2026
Ready to book your vacation to Kailua?
Kailua Hotel Deals
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
CA $264
CA $378 total
Sep 28 - Sep 29
includes taxes & fees
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
CA $236
CA $321 total
Sep 20 - Sep 21
includes taxes & fees
Courtyard Maui Kahului Airport
532 Keolani Place Kahului HI
Fully refundableReserve now, pay when you stay
CA $470
CA $558 total
Sep 22 - Sep 23
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"They lost power and have no back up."
Reviewed on Sep 2, 2026
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
Maui: Road to Hana Adventure with Farm to Table Lunch
CA $358
per adult
96% of travellers recommend
Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)
CA $66
per adult
100% of travellers recommend
Maui Beach Parks Self-Guided Driving Audio Tour
CA $21
per traveller
90% of travellers recommend
Frequently asked questions
How much does a Kailua vacation package cost?
You'll find cheap prices from CA $1,605 on Expedia for your Kailua getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Kailua costs.
What are the cheapest months to go to Kailua?
January, February and April are the best times to look for cheap Kailua vacation packages. Choosing to travel in quieter periods means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Kailua?
With a well-organized travel plan, you can easily hit the most popular Kailua sights in a handful of days. But if you want to discover lesser-known spots or take day trips, consider booking your Kailua vacation for longer.
How to find the best Kailua package deals?
Begin your search for a Kailua package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Kailua package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Kailua getaway off to a flying start.
Is it cheaper to book a Kailua vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can customize your Kailua trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
How to plan a trip to Kailua?
- Choose when to get away: Check your diary and get packing. Your preferred season and the activities on offer will also help you decide when to vacation in Kailua.
- Set a budget: Factor in costs like flights, food and transportation when working out how much to save for your trip to Kailua. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a lavish getaway.
- Decide how many days away: Start by making a list of all the attractions and activities you want to experience in Kailua. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Kailua vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
