Kailua Vacations from ¥74,941

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to ¥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Kailua Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kahana Villa
The Gardens at West Maui
Napili Kai Beach Resort
Royal Lahaina Resort & Bungalows
OUTRIGGER Kaanapali Beach Resort

Find the Best Kailua Vacation Packages

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 ¥35,003 per night from Jul 29 to Jul 30
¥35,003
¥44,745 total
Jul 29 - Jul 30
includes taxes & fees
8.8/10 Excellent! (1,217 reviews)
"Went there for work . I really enjoyed the hotel."

Reviewed on Jul 22, 2025

Maui Seaside Hotel
Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

3 out of 5
130 West Kaahumanu Avenue, Kahului, HI
Fully refundableReserve now, pay when you stay
The price is ¥44,689 per night from Aug 3 to Aug 4
¥44,689
¥57,034 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (60 reviews)
Highly Recommend 🌺
"Napua was the epitome of Aloha spirit and welcoming guests to Hawaii. From lei making, to the sunset ceremony, and her cheerful disposition, we were so impressed and loved our stay."

Reviewed on Jul 22, 2025

Hampton Inn & Suites Maui North Shore
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue, Kahului, HI
Fully refundableReserve now, pay when you stay
The price is ¥30,147 per night from Aug 12 to Aug 13
¥30,147
¥39,018 total
Aug 12 - Aug 13
includes taxes & fees
7.2/10 Good! (1,076 reviews)
"My husband and I stayed at this hotel for our honeymoon in Maui, and we had a wonderful experience. The staff was friendly and accommodating, helping us choose a room with an ocean view that we absolutely loved. The property is in a great location with stunning views."

Reviewed on Jul 22, 2025

Maui Beach Hotel
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

Frequently asked questions

How much does a Kailua vacation package cost?
You'll find cheap prices from ¥74,941 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?

  1. Choose your dates: What you want to do in Kailua and your preferred season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.