Kailua Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Kailua

Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
The price is S$423 per night from 22 Aug to 23 Aug
S$423
22 Aug - 23 Aug
includes taxes & fees
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
The price is S$337 per night from 6 Aug to 7 Aug
S$337
6 Aug - 7 Aug
includes taxes & fees
Maui Seaside 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 S$565 per night from 25 Aug to 26 Aug
S$565
25 Aug - 26 Aug
includes taxes & fees
9.2/10 Wonderful! (361 reviews)
"staff were so amazing. room staff were so thoughtful and went above and beyond."

Reviewed on 29 Jul, 2026

Hilton Grand Vacations Club Maui Bay Villas
See all 2,604 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

Maui Pineapple Farm Tour

Maui Pineapple Farm Tour

S$116
per adult
92% of travellers recommend
Maui Pineapple Farm Tour
Helicopter flying near sea cave in Hana

North Shore & Hana Rainforest Helicopter Tour with Taro Plantation Landing

S$516
per adult
96% of travellers recommend
North Shore & Hana Rainforest Helicopter Tour with Taro Plantation Landing
Maui Beach Parks Self-Guided Driving Tour

Maui Beach Parks Self-Guided Driving Audio Tour

S$19
per traveller
90% of travellers recommend
Maui Beach Parks Self-Guided Driving Audio Tour
See all activities in Kailua

Frequently asked questions

How much does a Kailua holiday package cost?
You'll find cheap prices 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.