Kailua Vacations from ￥220,456
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The Latest Kailua Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Aston Maui Hill
South Kihei
￥243,044
per person
Nov 2 - Nov 6
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
9/10 Wonderful! (950 reviews)
The property we stayed in was REALLY outdated. It was spacious, which was nice but the carpet was extremely old and all the furniture and bedding looked like it was from the 90’s. We came back to the place on 2 different days to dead cockroaches on the floor, not sure if that’s common here but it didn’t make us feel great. They keep the AC off prior to your stay so the condo took a long time to get cooled down from the heat.
The bed was comfortable, the pillows were terrible but I didn’t have a problem sleeping there.
Some others from our group had all tile instead of old carpet so maybe they update some and leave others alone.
I wouldn’t stay here again, it didn’t feel clean and for the price, I would look at different options.
The staff was mostly nice, I didn’t have a great experience with Rose at first but we came back later and James was great and professional.
Reviewed on Aug 19, 2026
Find the Best Kailua Vacation Packages
Kailua Hotel Deals
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
￥29,435
￥42,331 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (2,652 reviews)
"Clean room, balcony overlooking the pool. Nice comfy bed and beautiful bathroom."
Reviewed on Aug 19, 2026
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
￥30,186
￥40,571 total
Aug 31 - Sep 1
includes taxes & fees
8.8/10 Excellent! (1,568 reviews)
"The proximity to the airport is a positive. The front desk staff person who checked us in was very friendly. We were given a key card to a room that was already occupied. We opened our hotel room (late at night), and saw children in the room/ that the room was already occupied . This was honestly ..."
Reviewed on Aug 19, 2026
Hilton Grand Vacations Club Maui Bay Villas
575 S Kihei Road Kihei HI
￥54,067
￥69,826 total
Aug 27 - Aug 28
includes taxes & fees
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
Road to Hana Maui Tour: Self-Guided Audio Drive
￥2,712
per traveler
84% of travellers recommend
Maui: Lauhala Bracelet Weaving Craft Class
￥5,427
per adult
100% of travellers recommend
Maui Beach Parks Self-Guided Driving Audio Tour
￥2,393
per traveler
90% of travellers recommend
Frequently asked questions
How much does a Kailua vacation package cost?
You'll find cheap prices from ￥220,456 on Expedia for your Kailua break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Kailua costs.
What are the cheapest months to go to Kailua?
If you're looking to snag a cheap Kailua vacation package, consider planning a trip in January, February and April. You'll typically find better rates on hotels and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Kailua?
Usually, a handful of days is enough to explore the main attractions during your Kailua vacation. However, if you'd like to have more time to relax or take day trips, consider extending your itinerary.
How to find the best Kailua package deals?
Start your search for a Kailua package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Kailua package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Kailua escape underway.
Is it cheaper to book a Kailua vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still have the freedom to create a personalized Kailua vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Kailua?
If you're planning an impromptu Kailua getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Kailua?
- Choose your dates: What you want to do in Kailua and your preferred season will help you decide when to travel.
- Plan your budget wisely: As well as the cost of your stay, you should factor in other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could arise during your trip to Kailua.
- Determine how many days away: Start by compiling a list of the activities and sights you'd like to experience in Kailua. Then, estimate how long you'll need at each, along with any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Kailua vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
