Kailua Vacations from ￥46,981

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The Latest Kailua Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 28
found 22 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.4/10 Very Good! (488 reviews)
Safe Quiet neighborhood that is close to some of the most beautiful beaches. Property itself had a nice pool and condos were well equipped. Roosters were annoying in the morning but no fault of the property.

Reviewed on Aug 8, 2025

Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 28
found 22 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.6/10 Excellent! (192 reviews)
We loved our stay here. Our ocean view room was phenomenal. The only negative was no air conditioning but other than that we truly enjoyed our stay.

Reviewed on Aug 7, 2025

Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 28
found 22 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.2/10 Very Good! (438 reviews)
I liked the size of our dwelling and the ocean view is phenomenal!!

Reviewed on Jul 14, 2025

Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 28
found 22 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
I loved the resort, our room, and the beauty of Napili Bay. It had ultimate Hawaii feel and beauty. I snorkelled with multiple turtles each day. The waters were very clear. The whole area was very peaceful and family friendly. Recommend to any ocean or Hawaii lover.

Reviewed on Jul 31, 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 28
found 22 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.4/10 Very Good! (1,401 reviews)
Amazing view, room at a great price

Reviewed on Aug 7, 2025

Find the Best Kailua Vacation Packages

Kailua Hotel Deals

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 ￥29,852 per night from Aug 21 to Aug 22
￥29,852
￥38,681 total
Aug 21 - Aug 22
includes taxes & fees
7.2/10 Good! (1,084 reviews)
"Nice"

Reviewed on Aug 5, 2025

Maui Beach Hotel
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

4 out of 5
575 S Kihei Road, Kihei, HI
The price is ￥53,582 per night from Sep 1 to Sep 2
￥53,582
￥68,405 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (167 reviews)
"It was great . Polite people."

Reviewed on Jul 30, 2025

Hilton Grand Vacations Club Maui Bay Villas
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 ￥36,096 per night from Sep 6 to Sep 7
￥36,096
￥46,045 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (1,207 reviews)
"Maui Seaside Hotel is a good value. All the staff members were very friendly. We especially liked how walkable it is to the mall, the theater, and a bakery."

Reviewed on Aug 6, 2025

Maui Seaside Hotel
See all 2,271 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.

What to do in Kailua

Kahului: Self-Driving Audio Tour of Road to Hana

Road to Hana Maui Tour: Self-Guided Audio Drive

￥2,509
per traveler
82% of travellers recommend
Road to Hana Maui Tour: Self-Guided Audio Drive
Orchid Lei

Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)

￥6,998
per adult
100% of travellers recommend
Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)
Maui Beach Parks Self-Guided Driving Tour

Maui Beach Parks Self-Guided Driving Audio Tour

￥2,214
per traveler
80% of travellers recommend
Maui Beach Parks Self-Guided Driving Audio Tour
See all activities in Kailua

Frequently asked questions

How much does a Kailua vacation package cost?
You'll find cheap prices from ￥46,981 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.