
Kailua Holidays
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Top Flight + Hotel Deals in Kailua
Price found within the past 48 hours. Click for updated prices.

The Westin Maui Resort & Spa, Ka'anapali
Price was €2,519, price is now €2,363 per person
€2,363
per person
9 Jun - 14 Jun
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
9.2/10 Wonderful! (1,009 reviews)
It’s an old building that has been remodeled but it’s not all that. Could be better for it’s name “Weston.”
Reviewed on 14 Apr 2026

Fairmont Kea Lani Maui
Wailea
Price was €4,225, price is now €3,141 per person
€3,141
per person
9 Jun - 14 Jun
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Very beautiful property overall and great location! The one bedroom suite was perfect for our family of 4 with two teens. Really loved the restroom in our suite. Huge and had some nice upgrades like motion censored lights when you entered. The outside walking path was wonderful along the coast, and we took advantage of that. Staff was extremely helpful and I left a ballcap one day at the beach and one of the beach staff members kept it safe for me. Our 16 year old also lost her AirPod case which thankfully was personalized and the hotel found that for us as well. The free shuttle service to other nearby resorts and dinner spots was great. The staff at Pilina was terrific. The Pizza in the market was a hit and our teens enjoyed it multiple times. The server at Ko was great and high energy and helped customize our meal choices. Some areas for improvement- the hotel did not offer any fresh green juices. We like to have those in the morning at breakfast and there wasn’t any on the entire premises. Also, the cabanas were all in loud areas around the main pools with kids screaming in the pool and throwing balls that were hitting our chairs. We reserved 4 days of cabanas and finally cancelled day 4 because they just weren’t relaxing in the locations they were placed in. We have a 16 and 17 year old and when we booked the 4 cabanas we asked to book them at the adult pool but were told no since our kids aren’t 18. Terrible. Our kids are quiet so this was a miss. Great trip otherwise!
Reviewed on 11 Apr 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
Price was €4,279, price is now €3,314 per person
€3,314
per person
9 Jun - 14 Jun
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
8.8/10 Excellent! (1,001 reviews)
Perfect location for day drinking
Reviewed on 14 Apr 2026

The Ritz-Carlton Maui, Kapalua
Price was €3,062, price is now €2,738 per person
€2,738
per person
9 Jun - 14 Jun
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
9.2/10 Wonderful! (1,002 reviews)
Felt more like a Marriott than a Ritz. Hotel is okay, pool heater was out for the week, room was somewhat worn, AC was noisy. Not the same level of Ritz or Four Season's for the cost that I expect. Not a bad experience but not worth the cost compared to other 5 stars. I would not stay there again.
Reviewed on 15 Apr 2026

Four Seasons Resort Maui at Wailea
Wailea
Price was €4,813, price is now €4,400 per person
€4,400
per person
9 Jun - 14 Jun
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Kahului (OGG)
9.6/10 Exceptional! (1,000 reviews)
Wonderful Hotel Great restaurants staffed by true professionals
Reviewed on 14 Apr 2026
Top hotels in Kailua

Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
The price is €274 per night from 5 May to 6 May
€274
5 May - 6 May
includes taxes & fees
9.6/10 Exceptional! (2,572 reviews)
The room was immaculate. I stayed in the tower, looking over the pool and have an ocean view which was definitely worth the upgraded price. The staff is so incredibly kind and genuine. I was overly impressed when I come back. I’m only staying here from now on.
Reviewed on 16 Apr 2026

Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
The price is €238 per night from 10 May to 11 May
€238
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (1,357 reviews)
Excellent service, nice pool my daughter loves it! The room is clean and quiet. Beds are comfortable! Beach view. Very nice hotel will be back again someday
Reviewed on 16 Apr 2026

Maui Beach Hotel
170 W Kaahumanu Avenue Kahului HI
Fully refundableReserve now, pay when you stay
The price is €217 per night from 5 May to 6 May
€217
5 May - 6 May
includes taxes & fees
7.4/10 Good! (1,213 reviews)
Not as advertised. The room and hallway reeked of smoke. They couldn’t offer the shuttle to airport as advertised. Doors did not lock to access the wing of the property. We had to switch hotels because of the false advertising and general conditions.
Reviewed on 15 Apr 2026
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: Road to Hana Adventure with Farm to Table Lunch
€225
per adult
92% of travellers recommend

Maui Beach Parks Self-Guided Driving Audio Tour
€12
per traveller
90% of travellers recommend

West Maui Mountain Waterfall and Ocean Tour via Horseback
€163
per adult
90% of travellers recommend
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