Kailua Vacations

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Kailua Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Gods Peace Of Maui

Gods Peace Of Maui

$955
per person
Oct 1 - Oct 9
found 13 hours ago
Roundtrip flight included
Seattle (SEA) to Kahului (OGG)
Stay at this B&B in Makawao. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Haliʻimaile Farmer's Market and Hui Noʻeau Visual Arts Center are located nearby.
Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
Save 100% on your flight
$1,701
per person
Oct 1 - Oct 9
found 13 hours ago
Roundtrip flight included
Seattle (SEA) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are located nearby.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
Save 100% on your flight
$1,210
per person
Oct 1 - Oct 9
found 13 hours ago
Roundtrip flight included
Seattle (SEA) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
Signature Residences at Maui Banyan

Signature Residences at Maui Banyan

South Kihei
$1,693
per person
Sep 20 - Sep 25
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Book a stay at this business-friendly condo in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
The room was listed as a two bedroom, I expected it to be a single unit but management emailed me to notify that the booking was for two separate units right next to each other. It worked out well for us because we were a group of two families. Aside from that the unit was very clean, and spacious. I loved that it was right across from the beach ! The field next to us had deer! Which was an awesome surprise! The unit came equipped with all the cooking equipment, we were able to make breakfast and dinner which was a huge money saver. I also loved that they provided water filters so we didn’t have to spend the extra money on drinking water! I would book here again.

Reviewed on Aug 6, 2026

Lahaina Shores Beach Resort By Castle

Lahaina Shores Beach Resort By Castle

$1,570
per person
Sep 20 - Sep 25
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Book a stay at this beach apartment in Lahaina. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
$3,217
per person
Sep 20 - Sep 25
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
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Kailua Vacation Packages

Trying to figure out a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Kailua vacation packages can help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Kailua incredible. In just a few clicks, you can select the best Kailua vacation package for you and your family. We have an incredible list of flights and lodgings, as well as local things to do to pick from.

Hotel Deals in Kailua

Our listings include accommodations that are close to all the Kailua points of interest, and others that are just outside the city center for a quieter retreat.

We have competitive rates on everything from all-inclusive resorts that check off all the vacation must-haves to inexpensive hotels which are great for those on a budget. You can browse our vast catalog of options and pick the accommodation that is ideal for you and your family. With AARP Travel Center's Kailua hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.

Things to do in Kailua

People from all over make this city their vacation destination, and with good reason. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.

Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.

Book Together and Save

With so much happening in Kailua, you'll be wanting to plan your itinerary, not devoting time to finding the cheapest hotel. AARP Travel Center allows you to quickly get all you wish for, and save money at the same time. You can coordinate your entire vacation, including things to do in Kailua from only one site. The hardest packing you'll have to do is for your suitcase. Book now and save!

Top Hotel Deals

Maui Coast Hotel

Maui Coast Hotel

2259 S Kihei Rd Kihei HI
30.39 km from city center
Stay at this hotel in Kihei. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Maui Seaside Hotel

Maui Seaside Hotel

100 W Kaahumanu Ave Kahului HI
26.46 km from city center
Book a stay at this beach hotel in Kahului. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the restaurant in our ...
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

575 S Kihei Road Kihei HI
28.64 km from city center
Book a stay at this beach hotel in Kihei. Enjoy free parking, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. ...
Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

5031 Hana Hwy Hana HI
28.22 km from city center
Book a stay at this spa resort in Hana. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Maui Beach Hotel

Maui Beach Hotel

170 W Kaahumanu Avenue Kahului HI
26.72 km from city center
Book a stay at this beach hotel in Kahului. Enjoy a beach locale, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and ...
Courtyard Maui Kahului Airport

Courtyard Maui Kahului Airport

532 Keolani Place Kahului HI
24.34 km from city center
Book a stay at this business-friendly hotel in Kahului. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

130 West Kaahumanu Avenue Kahului HI
26.65 km from city center
Book a stay at this beach hotel in Kahului. Enjoy free breakfast, free WiFi, and a beach locale. Popular attractions Ho'aloha Park and Queen Ka’ahumanu Center ...
Gods Peace Of Maui

Gods Peace Of Maui

1290 Haliimaile Rd Makawao HI
12.27 km from city center
Stay at this B&B in Makawao. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Haliʻimaile Farmer's Market and Hui Noʻeau Visual Arts Center ...
Kohea Kai Hotel Maui

Kohea Kai Hotel Maui

551 S Kihei Rd Kihei HI
28.73 km from city center
Book a stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions ...
Maui Beach Vacation Club

Maui Beach Vacation Club

515 S. Kihei Road Kihei HI
28.66 km from city center
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
Maui Schooner Resort

Maui Schooner Resort

980 S Kihei Rd Kihei HI
29.3 km from city center
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
Maui Sunset

Maui Sunset

1032 S Kihei Rd Kihei HI
29.37 km from city center
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Wailea Beach and Waipuilani Park are located ...
Howzit Hostels

Howzit Hostels

2080 W Vineyard St Wailuku HI
29.94 km from city center
Stay at this hostel in Wailuku. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Paia Inn

Paia Inn

93 Hana Highway Paia HI
17.52 km from city center
Book a stay at this beach hotel in Paia. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hale Akua Garden Farm & Eco-Retreat

Hale Akua Garden Farm & Eco-Retreat

110 Door of Faith Rd Haiku HI
1.89 km from city center
Stay at this country house in Haiku. Enjoy free WiFi, free parking, and 4 beach bars. Popular attractions Twin Falls and Garden of Eden Arboretum are located ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Southwest Airlines
Southern Airways Express
Delta
United