Kailua Holidays from NZ$1,924

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The Latest Kailua Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
per person
2 Nov - 7 Nov
found 23 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
8.4/10 Very Good! (695 reviews)
The air conditioner didn't work our first 2 nights. We were moved the 3rd night but we were offered nothing for the inconvenience.

Reviewed on 13 Aug. 2025

Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
per person
2 Nov - 7 Nov
found 23 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
8.6/10 Excellent! (192 reviews)
The location was an hour away from the airport. However the drive was scenic and quiet. Some traffic depending on time and day of the week. The location was clean. The pool was small and had enough seating and resting benches. The view to the ocean was beautiful. No beach. We used the Gas bbq twice. It was clean and easy to use.

Reviewed on 16 Aug. 2025

Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
per person
2 Nov - 7 Nov
found 23 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
8/10 Very Good! (342 reviews)
Very old property, dark and dingy.

Reviewed on 12 Aug. 2025

Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
per person
2 Nov - 7 Nov
found 23 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
8.2/10 Very Good! (438 reviews)
The staff was nice. Captain jacks was really good. Rooms were extremely hot. No A/C. Some of the fans didn’t work. Property was clean but rooms were very very dated. Emma, the concierge, was AMAZING!

Reviewed on 14 Aug. 2025

Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
per person
2 Nov - 7 Nov
found 23 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
It’s absolutely beautiful and everyone is so kind!

Reviewed on 16 Aug. 2025

Kailua Holiday

Our pick of the best 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 NZ$445 per night from 24 Aug to 25 Aug
NZ$445
24 Aug - 25 Aug
includes taxes & fees
7.2/10 Good! (1,086 reviews)
"We enjoy staying at the Maui Beach Hotel. Its descent price, friendly staff, clean property....great to stay when popping in from the Big Island."

Reviewed on 12 Aug. 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 NZ$786 per night from 1 Sept to 2 Sept
NZ$786
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (174 reviews)
"Breath-taking property! Had a whole condo to ourselves, two beds and two full baths. Be careful, they try to sell you a timeshare and you have to attend a meeting that is half a day"

Reviewed on 7 Aug. 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 refundable
The price is NZ$461 per night from 23 Aug to 24 Aug
NZ$461
23 Aug - 24 Aug
includes taxes & fees
8.8/10 Excellent! (1,196 reviews)
"We had a nice enjoyable experience. Very friendly and helpful staff. Relaxing environment with very nice beach and pool."

Reviewed on 11 Aug. 2025

Maui Seaside Hotel
See all 2,270 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.

Discover the most popular places to visit in Kailua

Twin Falls

Twin Falls

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

What to do in Kailua

Fun zipping in the jungle.

Maui Zipline Eco Adventure: 8 Lines through the Jungle

NZ$273
per adult
100% of travellers recommend
Maui Zipline Eco Adventure: 8 Lines through the Jungle
Private Waterfall, Rainforest & Handcrafted Chocolate Tour

Haiku: Waterfall, Rainforest, and Handcrafted Chocolate Tour

NZ$213
per adult
100% of travellers recommend
Haiku: Waterfall, Rainforest, and Handcrafted Chocolate Tour
NorthShore Zipline Co 7-Line Tour

7-Line Maui Zipline on the North Shore

NZ$258
per adult
96% of travellers recommend
7-Line Maui Zipline on the North Shore
See all activities in Kailua

Frequently asked questions

How much does a Kailua holiday package cost?
You'll find cheap prices from NZ$1,924 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 holiday to Kailua costs.
What are the cheapest months to go to Kailua?
If you're looking to snag a cheap Kailua holiday 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 holiday. 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 holiday as a package?
Expedia holiday 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 personalised Kailua holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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 holiday 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.