Kailua Vacations from $1,311

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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.
Maui Beach Vacation Club
Hyatt Vacation Club at Ka'anapali Beach, Maui
Palms at Wailea Maui
Maui Banyan Vacation Club
Fairmont Kea Lani Maui
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Discover the most popular places to visit in Kailua

What to do in Kailua

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
$237 nightly
The price is $281 total per night from Apr 28 to Apr 29
$281 total
Apr 28 - Apr 29
Total with taxes and fees
8.8/10 Excellent! (1,356 reviews)
Jasmine and Fe were very helpful. Jasmine helped me out finding leis and Fe was very supportive of checking out. We will definitely be back. The staff was very friendly and helpful, grounds were clean and walking distance to a very calm beach, really great if you have little kids

Reviewed on Apr 11, 2026

Maui Seaside Hotel
Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
$272 nightly
The price is $323 total per night from May 5 to May 6
$323 total
May 5 - May 6
Total with taxes and fees
9.6/10 Exceptional! (2,575 reviews)
This hotel exceeded our expectations. The staff was very friendly and took us on the shuttle wherever we wanted to go. We would definitely book again.

Reviewed on Apr 13, 2026

Maui Coast Hotel
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue Kahului HI
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $257 total per night from May 13 to May 14
$257 total
May 13 - May 14
Total with taxes and fees
7.4/10 Good! (1,218 reviews)
Breakfast good for $20 adults, parking $26.xx, property fee $23.xx each night. Good amenities on the grass (corn hole, etc.), nice chairs by the ocean. Not much beach (rocky). Nice beach park 2.2 miles from the property. Low season probably in mid-April but not very busy. Overall recommend for a ...

Reviewed on Apr 14, 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 $1,311 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.