Kailua Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Kailua vacation package deals
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
9.4/10 Exceptional! (1,002 reviews)
Aug 28 - Aug 31
3 night stay
Denver (DEN) to Kahului (OGG)
Southwest Airlines • Non-stop • Coach
Kahului (OGG) to Denver (DEN)
Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,037, price is now $1,334 per person
$1,334
per person
found 1 day ago
Very serene, not crowded and no children. Perfect for an intimate getaway.
Reviewed on Mar 22, 2025
3.5-star property
Palms at Wailea Maui
Wailea
8.4/10 Very Good! (542 reviews)
Sep 7 - Sep 14
7 night stay
San Francisco (SFO) to Kahului (OGG)
Alaska Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,592, price is now $1,738 per person
$1,738
per person
found 20 hours ago
Our condo was beautiful the pool was great and the views were lovely. Exceeded all expectations, Would stay again.
Reviewed on Jun 27, 2026
5.0-star property
Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
8.8/10 Excellent! (1,017 reviews)
Sep 4 - Sep 11
7 night stay
Austin (AUS) to Kahului (OGG)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,372, price is now $3,044 per person
$3,044
per person
found 9 hours ago
Great place and beautiful. Pool is a dream for kids but prepare to pay an obscene amount for everything including the hilarious 20+ bucks for a basic peanut butter and jelly sandwich
Walls between rooms are thin for a fancy hotel. Can hear with crystal clarity what the people next door weee saying. Ceilings are well insulated on the other hand.
Also factor in all the “resort fees” (yes.. your room charge does not include using the pool for some reason) the taxes, and required valet parking fees (if you bring a car) and your nightly stay just increased 200 bucks a night for the room. So add this you what you see as the price per night.
Reviewed on Jun 2, 2026
2.5-star property
Kihei Surfside - Maui Condo & Home
South Kihei
8.6/10 Excellent! (69 reviews)
Sep 15 - Sep 22
7 night stay
Denver (DEN) to Kahului (OGG)
Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,962, price is now $1,377 per person
$1,377
per person
found 1 day ago
Beautiful, well kept, convenient location.
Reviewed on Jun 3, 2025
Top rated hotels for your Kailua vacation package
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Free Cancellation
Reserve now, pay when you stay
16.43 mi from city center
$195 nightly
The price is $232 total per night
$232 total
Jul 6 - Jul 7
Total with taxes and fees
Guests of Maui Seaside Hotel enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. If you drive, self parking is USD 26.18 per night, or you can take advantage of the free airport shuttle (available on request). The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a water dispenser and a vending machine.
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Free Cancellation
Reserve now, pay when you stay
18.87 mi from city center
$272 nightly
The price is $323 total per night
$323 total
Jul 20 - Jul 21
Total with taxes and fees
At Maui Coast Hotel, guests enjoy 2 outdoor pools, a children's pool, and a 24-hour gym. Parking is available for USD 20.94 per night (USD 26.18 per night for valet parking), and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with securing valuables and dry cleaning/laundry. Additional amenities include 3 hot tubs, free WiFi in public areas, and free use of bicycles.
Hilton Grand Vacations Club Maui Bay Villas
575 S Kihei Road Kihei HI
17.78 mi from city center
$409 nightly
The price is $485 total per night
$485 total
Jul 6 - Jul 7
Total with taxes and fees
Hilton Grand Vacations Club Maui Bay Villas features an outdoor pool, a children's pool, and a gym. There's free parking if you drive. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and securing valuables. Other amenities at this beach hotel include free WiFi in public areas, a free kid's club, and a terrace.
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.
Things to do
Road to Hana Maui Tour: Self-Guided Audio Drive
$17
per traveler
84% of travellers recommend
Maui: Road to Hana Adventure with Farm to Table Lunch
$259
per adult
94% of travellers recommend
Kahului Airport Custom Lei Greeting - Choose Your Lei (OGG)
$62
per child
94% of travellers recommend
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