Kailua Vacation Packages
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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.
Maui Schooner Resort
Central Kihei
CA $1,737
per person
Sep 20 - Sep 27
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Kahului (OGG)
9.2/10 Wonderful! (544 reviews)
We arrived at 10pm and office closed at 6, so we panicked a bit about how we could check in, but there is a phone on the wall outside the office to call the after hours security, and he was friendly and helpful, and got us our room keys (major relief!). Room is not fancy but very spacious, we had 2 bedroom, 2 bath condo. Giant bathroom and closet in master, nice king size bed, and black out curtains. Kitchen seemed to be well stocked with essentials but we didn’t use more than the fridge and coffee pot, which they did have basket filters and a few servings of coffee available (could purchase additional). Nice Tommy bahama beach chairs for use, and a cooler, which was a very useful bonus, in the room. In the office you can borrow snorkels, fins, boogie boards, etc for free- also super handy. Tennis court was in rough shape but lots of people out playing on it so I guess was still usable. Beach across from it was not one of those picturesque ones, so we didn’t hang out there more than a quick morning walk. Overall I would definitely stay there again for the price and value. Not too far from airport and other things in the local town- about 10min to grocery store, etc, but we didn’t actually hang around the area much.
Reviewed on Aug 7, 2026
Royal Lahaina Bungalows & Spa
CA $2,366
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
8/10 Very good! (22 reviews)
I had an absolutely fantastic stay at the Royal Lahaina Bungalows & Spa. Highly recommend this hotel if you are looking for a beautiful beach front hotel minus the large resort/casino vibes. I did a lot of research before booking to stay here and boy am I glad I did! Could not have been happier. Traveled with family and we stayed in two of the beachfront bungalows (building C) which were so comfortable, peaceful and the best views. There were always chairs available around the pools. The staff would set up an umbrella and chairs for us on the beach when we wanted. Happy hour had great drinks by the pool bar. Nightly musical entertainment was a bonus. All of the staff at the hotel were friendly and welcoming.
Reviewed on Aug 3, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
CA $5,100
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
This is a super nice adult only hotel. Nice and quiet. Staff is wonderful. On point. Hotel car service is excellent with luxury cars available. The room is nice. Large and spacious. My only critique is that the restaurant has a limited menu. But selection is great. Highly recommend.
Reviewed on Jul 25, 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 $309
CA $432 total
Aug 9 - Aug 10
includes taxes & fees
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
CA $245
CA $332 total
Aug 26 - Aug 27
includes taxes & fees
8.8/10 Excellent! (1,557 reviews)
"I did not like the added charges of $25 a day for pool, shuttle to golf, etc. that we did not need nor want or used. The help staff were excellent and friendly."
Reviewed on Aug 7, 2026
Hilton Grand Vacations Club Maui Bay Villas
575 S Kihei Road Kihei HI
CA $475
CA $614 total
Aug 22 - Aug 23
includes taxes & fees
9.2/10 Wonderful! (366 reviews)
"It is Amazing place to stay. Suites are big and very comfortable for families to stay. Great hotel."
Reviewed on Aug 6, 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 Beach Parks Self-Guided Driving Audio Tour
CA $21
per traveller
90% of travellers recommend
Haleakala Downhill Bike Tour Self-Guided Ride with Maui Sunriders
CA $195
per adult
90% of travellers recommend
Frequently asked questions
How much does a Kailua vacation package cost?
You'll find cheap prices from CA $1,737 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.
