Kailua Vacation Packages
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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.
Top Kailua Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club
North Kihei
Price was CA $2,631, price is now CA $1,787 per person
CA $1,787
per person
Jul 21 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very Good! (865 reviews)
Beautiful view and close to the beach. Would stay there again.
Reviewed on May 3, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Price was CA $7,554, price is now CA $4,811 per person
CA $4,811
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Everything was Amazing!! Will be coming back
Reviewed on Apr 18, 2026
Palms at Wailea Maui
Wailea
Price was CA $3,963, price is now CA $2,544 per person
CA $2,544
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
8.4/10 Very Good! (537 reviews)
Twin room had dirty sheets and place was swarmed with mosquitos.
Reviewed on May 2, 2026
Fairmont Kea Lani Maui
Wailea
Price was CA $8,461, price is now CA $6,141 per person
CA $6,141
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
BEAUTIFUL PROPERTY!! Worth every cent. The staff was first class and took care of our every need.
Reviewed on May 6, 2026
Grand Champions
Wailea
Price was CA $3,974, price is now CA $2,902 per person
CA $2,902
per person
Jun 26 - Jul 3
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
9.2/10 Wonderful! (5 reviews)
Grand Champions exceeded every expectation. The property is beautifully maintained with lush tropical landscaping that instantly sets the tone for a relaxing Maui getaway. The unit was spotless, well-appointed, and had everything we needed — the kitchen was fully equipped, the beds were comfortable, and the lanai was the perfect spot for morning coffee.
The location in Wailea is unbeatable: quiet and private, yet minutes from world-class beaches, restaurants, and Shops at Wailea. The pools were pristine and never crowded, and the grounds feel more like a resort than a condo complex.
Check-in was seamless and communication with the host was prompt and professional throughout. We’d absolutely stay here again and recommend it to anyone looking for a comfortable, upscale base to explore South Maui. Mahalo!
Reviewed on Apr 20, 2026
Kailua Hotel Deals
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
The price is CA $331 per night from May 25 to May 26
CA $331
CA $456 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (2,587 reviews)
The hotel was very clean and well kept. The staff was helpful and nice. We used the shuttle service for trips to restaurants and shopping, which allowed us to not have to worry about finding parking.
Reviewed on May 8, 2026
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
The price is CA $298 per night from May 30 to May 31
CA $298
CA $395 total
May 30 - May 31
includes taxes & fees
8.8/10 Excellent! (1,404 reviews)
Goodn
Reviewed on May 8, 2026
Maui Beach Hotel
170 W Kaahumanu Avenue Kahului HI
The price is CA $289 per night from May 25 to May 26
CA $289
CA $376 total
May 25 - May 26
includes taxes & fees
7.4/10 Good! (1,238 reviews)
Central location
Reviewed on May 8, 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 Beach Parks Self-Guided Driving Audio Tour
CA $19
per traveller
90% of travellers recommend
Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)
CA $65
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
