Olowalu Vacations

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Olowalu Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Signature Residences at Maui Banyan

Signature Residences at Maui Banyan

South Kihei
Save 100% on your flight
$880
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip flight included
Honolulu (HNL) 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.
It was as good as a motel 6 bed was comfortable and my beach front condo as it was described was a room facing a mountain that you couldn’t see passed the forest of plants in front of back patio and the ac unit was very old and loud but served its purpose

Reviewed on Sep 21, 2026

The Ocean View Residence

The Ocean View Residence

South Kihei
Save 100% on your flight
$956
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
Book a stay at this beach apartment in Kihei. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Wailea Beach and Charley Young Beach are located nearby.
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Reviewed on Sep 28, 2026

Hotel Wailea Maui

Hotel Wailea Maui

Wailea
Save 100% on your flight
$4,313
per person
Nov 30 - Dec 5
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
$972
per person
Nov 30 - Dec 5
found 19 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) 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.
Kamaole Sands - Maui Condo & Home

Kamaole Sands - Maui Condo & Home

South Kihei
Save 100% on your flight
$940
per person
Nov 17 - Nov 22
found 21 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
Book a stay at this beach condo in Kihei. Enjoy a beach locale, a 24-hour front desk, and 4 outdoor tennis courts. Popular attractions Wailea Beach and Kamaole Beach Park 3 are located nearby.
Overall solid for the price. Old inside

Reviewed on Oct 5, 2026

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
$2,653
per person
Nov 30 - Dec 5
found 19 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) 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.
The staff were amazing, evening room service was excellent surprise

Reviewed on Oct 6, 2026

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Olowalu Vacation Packages

Looking for ways save money and time on your next holiday to Olowalu? The AARP Travel Center Powered by Expedia® can help you do both. 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 Olowalu perfect. In just a few clicks, you can select the best Olowalu vacation package for you. We have a huge list of flights and hotels, as well as Olowalu things to do to choose from.

Olowalu Hotels

With 13584 hotels and resorts in Olowalu to choose from, you will find one that is perfect for you.

From Olowalu hotels with swimming pools and on-site restaurants, to boutique accommodations that add all the thoughtful touches, you'll find a hotel here that will make your trip one to remember. With AARP Travel Center's Olowalu hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.

Things to do in Olowalu

Olowalu is the ideal spot when you need to get away from it all. With only around 69 people here, this hidden-gem is great for a quite vacation.

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

Save with a Olowalu Vacation Package

As an AARP Member, you get to cash in on all the great savings. You'll save on select hotels worldwide, flights, and even rental cars. No matter what vacation package you select, you can rest easy knowing that you already saved on your trip. The hardest packing you'll have to do is for your suitcase. Bundle now and get ready for your Olowalu vacation.

Top Hotel Deals

Aston Kaanapali Shores

Aston Kaanapali Shores

3445 Lower Honoapiilani Hwy Lahaina HI
16.92 km from city center
Book a stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in ...
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI
23.77 km from city center
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI
15.19 km from city center
Book a stay at this beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Maui Coast Hotel

Maui Coast Hotel

2259 S Kihei Rd Kihei HI
20.75 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 ...
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI
14.19 km from city center
Book a stay at this luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property ...
Maui Seaside Hotel

Maui Seaside Hotel

100 W Kaahumanu Ave Kahului HI
18.09 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 ...
Maui Beach Hotel

Maui Beach Hotel

170 W Kaahumanu Avenue Kahului HI
17.83 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 ...
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI
24.22 km from city center
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 ...
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

2525 Kaanapali Parkway Lahaina HI
14.55 km from city center
Book a stay at this beach resort in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI
23.33 km from city center
Book a stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI
13.96 km from city center
Book a stay at this beach resort in Kaanapali. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property ...
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

110 Ka'anapali Shores Place Kaanapali HI
16.64 km from city center
Book a stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition ...
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

575 S Kihei Road Kihei HI
17.85 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. ...
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI
21.27 km from city center
Book a stay at this luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

45 Kai Ala Dr Lahaina HI
15.4 km from city center
Book a stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
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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.

Southern Airways Express
Alaska Airlines
Southwest Airlines
Delta
Tue, Jan 19 - Wed, Jan 20
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$290
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Jan 19 from Norman Y. Mineta San Jose Intl. to Kahului, returning Wed, Jan 20, priced at $290 found 21 hours ago
United