Kailua Vacations from $1,360
Book a Hotel + Flight or Car together to unlock savings
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.
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
$2,986
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,006 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards!
Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches.
The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool!
The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X
Reviewed on Sep 6, 2026
What to do in Kailua
Road to Hana Maui Tour: Self-Guided Audio Drive
$17
per traveler
84% of travellers recommend
Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)
$47
per adult
100% of travellers recommend
Kahului Airport Custom Lei Greeting - Choose Your Lei (OGG)
$62
per child
94% of travellers recommend
Kailua Hotel Deals
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
$229 nightly
$272 total
Sep 28 - Sep 29
Total with taxes and fees
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
$205 nightly
$243 total
Sep 13 - Sep 14
Total with taxes and fees
8.8/10 Excellent! (1,586 reviews)
"😍😍😍😍"
Reviewed on Sep 7, 2026
Courtyard Maui Kahului Airport
532 Keolani Place Kahului HI
Fully refundableReserve now, pay when you stay
$339 nightly
$402 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"They charged my overnight parking 2 times. At check-in on 9/1 $40 for 2-nights parking. And again they charged me $20 each night on the 9/1 & 9/2. Around 8:30pm there was a humming sound for about an hour. It was coming from the wall between 224 & 226 by the corner along the exterior wall. The loud ..."
Reviewed on Sep 7, 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.
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 $1,360 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.