Kailua Vacations from $1,336

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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 Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Save 100% on your flight
Price was $2,215, price is now $1,336 per person
$1,336
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8/10 Very Good! (370 reviews)
Room is clean with full kitchen, nice beaches just across the road

Reviewed on May 28, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was $4,308, price is now $2,473 per person
$2,473
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
Everything was Amazing!! Will be coming back

Reviewed on Apr 18, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $2,761, price is now $1,671 per person
$1,671
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (872 reviews)
Clean, bottom floor, so not much of an ocean view but easily walk out to sit poolside I would recommend and I come back to stay

Reviewed on Jun 1, 2026

Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Save 100% on your flight
Price was $2,870, price is now $1,784 per person
$1,784
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (539 reviews)
Was great, very spacious and a great stay

Reviewed on May 25, 2026

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $5,744, price is now $4,005 per person
$4,005
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
The resort was excellent and made for a great trip!

Reviewed on May 31, 2026

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Discover the most popular places to visit in Kailua

Twin Falls

4.5/5(69 reviews)

Commune with nature and explore the great outdoors at Twin Falls during your travels in Haiku. While you're in the area, stroll along the beautiful beaches.

Twin Falls

Haiku Park

Explore the great outdoors at Haiku Park, a lovely green space in Pauwela. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Haiku Park

Haleakala Bike Company

You can take time to visit Haleakala Bike Company during your travels to Pauwela. Wander the beautiful beaches and seaside in the area.

Haleakala Bike Company

What to do in Kailua

Kahului: Self-Driving Audio Tour of Road to Hana

Road to Hana Maui Tour: Self-Guided Audio Drive

$15
per traveler
82% of travellers recommend
Road to Hana Maui Tour: Self-Guided Audio Drive
Maui Zipline Eco Adventure: 8 Lines through the Jungle

Maui Zipline Eco Adventure: 8 Lines through the Jungle

$177
per adult
100% of travellers recommend
Maui Zipline Eco Adventure: 8 Lines through the Jungle
Maui Pineapple Farm Tour

Maui Pineapple Farm Tour

$99
per adult
92% of travellers recommend
Maui Pineapple Farm Tour
See all activities 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
$279 nightly
The price is $332 total per night from Jun 28 to Jun 29
$332 total
Jun 28 - Jun 29
Total with taxes and fees
9.6/10 Exceptional! (2,608 reviews)
"Clean room, accessible water station, friendly staff"

Reviewed on Jun 1, 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
$179 nightly
The price is $212 total per night from Jul 3 to Jul 4
$212 total
Jul 3 - Jul 4
Total with taxes and fees
8.8/10 Excellent! (1,434 reviews)
"Great hotel, would stay again. The bed was comfortable! Room was clean and the staff were very friendly."

Reviewed on Jun 1, 2026

Maui Seaside Hotel
Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

4 out of 5
5031 Hana Hwy Hana HI
Fully refundableReserve now, pay when you stay
$434 nightly
The price is $515 total per night from Jun 3 to Jun 4
$515 total
Jun 3 - Jun 4
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Amazing resort, staff are incredible, views are outstanding. Everything was included in nightly fees, beds were very comfortable. Cannot wait to come back to Hana just to enjoy the serenity of this place."

Reviewed on May 31, 2026

Hana-Maui Resort, a Destination by Hyatt Residence
See all 2,610 properties in Kailua
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 $1,336 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.