Kailua Vacations from $757

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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.
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,275, price is now $757 per person
$757
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9/10 Wonderful! (1,384 reviews)
The room was clean, the property was gorgeous. The breakfast staff was super great. Took 30 minutes to check in and the staff was rude. Parking & resort fees were added to our expedia total.

Reviewed on Oct 21, 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was $3,871, price is now $2,154 per person
$2,154
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (1,500 reviews)
Very clean, great staff, will visit again...A++++

Reviewed on Oct 22, 2025

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,368, price is now $773 per person
$773
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9/10 Wonderful! (1,675 reviews)
Peaceful, beautiful location felt like home

Reviewed on Oct 24, 2025

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $4,548, price is now $2,583 per person
$2,583
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Kahului (OGG)
8.2/10 Very Good! (802 reviews)
A excelent service in the office. Nice and clean room y all the hotel. I recommend this hotel.

Reviewed on Oct 22, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was $7,138, price is now $4,102 per person
$4,102
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!

Reviewed on Aug 27, 2025

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Discover the most popular places to visit in Kailua

Tropical Paradise After hiking along the meandering path, past the bamboo forest and crossing the often times dangerous creek, we came across this stunning waterfall amphitheatre and amazing approach. We were not prepared for a swim but doffed what we could and swam anyways. Definitely a bucket list moment.

Twin Falls

4.5/5(68 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

$17
per traveler
84% of travellers recommend
Road to Hana Maui Tour: Self-Guided Audio Drive
Authentic Lei Greeting at Kahului Airport

Authentic Lei Greeting at Kahului Airport

$62
per child
90% of travellers recommend
Authentic Lei Greeting at Kahului Airport
Maui Horseback Adventure at Circle M Ranch With Real Cowboys

Maui Horseback Adventure at Circle M Ranch With Real Cowboys

$185
per adult
100% of travellers recommend
Maui Horseback Adventure at Circle M Ranch With Real Cowboys
See all activities in Kailua

Kailua Hotel Deals

Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
100 W Kaahumanu Ave, Kahului, HI
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $250 total per night from Nov 2 to Nov 3
$250 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,171 reviews)
Great staff

Reviewed on Oct 20, 2025

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
$369 nightly
The price is $435 total per night from Oct 31 to Nov 1
$435 total
Oct 31 - Nov 1
Total with taxes and fees
9/10 Wonderful! (206 reviews)
Clean room, lots of space quiet

Reviewed on Oct 16, 2025

Hilton Grand Vacations Club Maui Bay Villas
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue, Kahului, HI
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $253 total per night from Nov 2 to Nov 3
$253 total
Nov 2 - Nov 3
Total with taxes and fees
7.2/10 Good! (1,111 reviews)
Great staff

Reviewed on Oct 19, 2025

Maui Beach Hotel
See all 2,277 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 $757 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.