Kailua Vacations from $738

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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.

The Latest Kailua vacation packages

Price found within the past 48 hours. Click for updated prices.
Kahana Beach Vacation Club
Mana Kai Maui- Official Onsite Rental
Kahana Villa
Hotel Wailea, Relais & Chateaux - Adults Only
Maui Banyan Vacation Club
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Discover the most popular places to visit in Kailua

What to do in Kailua

Kailua Hotel Deals

Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $349 total per night from Jan 27 to Jan 28
$349 total
Jan 27 - Jan 28
Total with taxes and fees
9.4/10 Exceptional! (2,385 reviews)
Everything about this hotel is fantastic. Staff, service, amenities. I would definitely book here again without hesitation. The location is incredible.

Reviewed on Jan 8, 2026

Maui Coast Hotel
Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $301 total per night from Jan 25 to Jan 26
$301 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (1,220 reviews)
The room was clean and perfect for an overnight stay when our flight was canceled. The cool cloths while we waited in line were a great touch!

Reviewed on Jan 6, 2026

Maui Seaside Hotel
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue Kahului HI
Fully refundableReserve now, pay when you stay
$232 nightly
The price is $275 total per night from Jan 19 to Jan 20
$275 total
Jan 19 - Jan 20
Total with taxes and fees
7.2/10 Good! (1,145 reviews)
Yes! This hotel fully met my needs after a very long, tediuous flight from South Dakota. Just used it to adjust to a different time zone and get some rest. This Hotel met all my criteria and I would recommend it after a long day of traveling from the Mainland to Hawaii.

Reviewed on Jan 10, 2026

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.

Find the Best Kailua Vacation Packages

Kailua Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Kahului Airport (OGG)
Max Temp Winter
75ºF
Max Temp Summer
80ºF
Top Sights
Twin Falls and Haiku Park

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Frequently asked questions

How much does a Kailua vacation package cost?
You'll find cheap prices from $738 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?
You can typically find lower prices and better availability in September, October and December. Browse our cheap Kailua vacation packages and you could land some excellent off-season deals.
How many days is enough for Kailua?
The ideal duration for your Kailua vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to go to all the main sights and discover some hidden gems along the way.
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.
Does Expedia offer Book Now, Pay Later Kailua vacation packages?
Your Kailua trip should be an escape from your busy life, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.