Wailea-Makena Vacations from ￥126,166

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The Latest Wailea-Makena Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was ￥220,848, price is now ￥126,166 per person
￥126,166
per person
Mar 2 - Mar 7
found 2 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.2/10 Very Good! (814 reviews)
Very clean, great staff. Pool was nice, good location. Living room furniture uncomfortable.

Reviewed on Jan 16, 2026

Kahana Villa

Kahana Villa

3 out of 5
Price was ￥250,974, price is now ￥129,834 per person
￥129,834
per person
Mar 2 - Mar 7
found 2 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8/10 Very Good! (351 reviews)
This place was absolutely amazing! The location was fantasic, the view was beautiful and the two bedroom villa far exceeded my expectations! I will be back and I know exactly where I want to stay!

Reviewed on Jan 6, 2026

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was ￥263,992, price is now ￥138,429 per person
￥138,429
per person
Mar 2 - Mar 7
found 2 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8/10 Very Good! (351 reviews)
Bed was uncomfortable.

Reviewed on Jan 11, 2026

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
South Kihei
Save 100% on your flight
Price was ￥432,549, price is now ￥232,673 per person
￥232,673
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
8.8/10 Excellent! (1,002 reviews)
The good: Beach is amazing including the snorkeling. Store has everything you need, a little more expensive but not ridiculous. The bad: weird check-in and service. The rooms are obviously managed by different companies. Front desk isn't necessarily your main contact. They call someone else. The 'B' rooms are tiny......only enough room to sleep. No ice....have to buy it for $5 per bag at the store. Overall, we'd come back to this area but not sure if we would do the 'B' room.

Reviewed on Jan 10, 2026

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was ￥312,194, price is now ￥175,138 per person
￥175,138
per person
Mar 2 - Mar 7
found 2 hours ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9/10 Wonderful! (1,465 reviews)
All the staff was super friendly and helpful. The propert was immaculate and very easy access to the beach!

Reviewed on Jan 16, 2026

Find the Best Wailea-Makena Vacation Packages

Wailea-Makena Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
The price is ￥112,282 per night from Jan 29 to Jan 30
￥112,282
￥143,580 total
Jan 29 - Jan 30
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
This property is amazing and you should definitely experience it! Only downside is that every single thing is paid. They have made it so that you can’t experience ever unless you book 3 days in any case so your research and be prepared to pay extra fees for all experiences

Reviewed on Jan 14, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
The price is ￥126,079 per night from Jan 18 to Jan 19
￥126,079
￥160,025 total
Jan 18 - Jan 19
includes taxes & fees
9.6/10 Exceptional! (999 reviews)
Service was good

Reviewed on Jan 8, 2026

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is ￥150,843 per night from Feb 6 to Feb 7
￥150,843
￥188,482 total
Feb 6 - Feb 7
includes taxes & fees
9.4/10 Exceptional! (1,011 reviews)
Fantastic experience all around.

Reviewed on Jan 7, 2026

Fairmont Kea Lani Maui
See all 2,940 properties in Wailea-Makena
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.

Discover the most popular places to visit in Wailea-Makena

Wailea Beach showing tropical scenes, swimming and a sandy beach

Wailea Beach

This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.

Wailea Beach
Keawakapu Beach which includes tropical scenes, general coastal views and a hotel

Keawakapu Beach North

Enjoy the peace and quiet at one of Maui’s less crowded and wider beaches, where kids can wander around the rock pools, and divers can explore the artificial reef.

Keawakapu Beach North
Kamaole Beach Park 3

Kamaole Beach Park 3

During your trip to Kihei, enjoy the surf and sand at Kamaole Beach Park 3 along with the snorkeling. Wander the seaside or discover the beautiful sunsets in this family-friendly area.

Kamaole Beach Park 3

What to do in Wailea-Makena

Humpback Whale spouts a rainbow off West Oahu

Semi-Private Boat Tours for Humpback Whale Watching in West Oahu

￥29,748
per adult
Semi-Private Boat Tours for Humpback Whale Watching in West Oahu
Bee Farm Ecotour and Honey Tasting in Waialua, North Shore Oahu

Bee Farm Ecotour and Honey Tasting in Waialua, North Shore Oahu

￥21,137
per adult
Bee Farm Ecotour and Honey Tasting in Waialua, North Shore Oahu
West Oahu Whale Watching & Turtle Snorkeling

Whale & Dolphin Watching, Turtle Snorkeling

￥26,067
per adult
100% of travellers recommend
Whale & Dolphin Watching, Turtle Snorkeling
See all activities in Wailea-Makena

Frequently asked questions

Can I cancel my flight booking to Wailea-Makena due to COVID-19?
In these challenging times, many airlines are offering more flexibility. Go to our Customer Service Portal for useful information about amending or canceling your booking due to COVID-19.
What's the best way to find cheap flights to Wailea-Makena that have flexible change policies?
At Expedia, we've been channeling our inner contortionist to get you the most flexible fares in town. Just tick the "No change fee" box directly below the filter subheading "Flexible change policies" to find the best flights to Wailea-Makena.
What are some of the general tips for travelers to Wailea-Makena during the COVID-19 outbreak?
With new rules, restrictions and safety measures to follow, travel looks a lot different nowadays. Here's what you should know before you get on that plane to Wailea-Makena:
  • Before committing to anything, see if any travel restrictions apply — in both your origin and destination. Keep informed with the latest updates by checking government travel advisories.
  • Keep your face mask on even during airport screening. A TSA officer will ask you to adjust your mask for identification purposes.
  • To minimize the risk of cross-contamination, place your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA employee.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be taken out for X-ray scanning.
  • Place any personal items (keys, wallet and phone) in your carry-on rather than a bin to reduce handling during the screening process.
  • Separate any food you have for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA agent to touch and inspect your belongings.

Which airlines fly to Wailea-Makena?
Let Hawaiian Airlines take you there. This well-known carrier operates 1202 flights every month to Kahului Airport (OGG), a Wailea-Makena gateway.
How can I find cheap tickets to Wailea-Makena?
You'll always walk away with a fabulous deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred travel date, then click on the flexible dates box above to see a list of prices for nearby days. was the lowest price for a flight to Wailea-Makena in the last seven days.
How much is a flight to Wailea-Makena?
If you were jetting one way from (), you could've nabbed a cheap fare for just in the last seven days. Round-trip flights to Wailea-Makena ranged from only to during this same period.
What are the most popular airports to fly into in Wailea-Makena?
Kahului Airport (OGG) is the main point of entry for many headed to Wailea-Makena. Approximately 3826 flights every month touch down at this airport.
When is the cheapest time to fly to Wailea-Makena?
Consider jetting off earlier in the week to nab the best deal to Wailea-Makena. Tuesday is generally the most economical day to depart, followed by Monday. Saturday often has the highest fares. This is because a lot of travelers prefer to start their break on a weekend.
How much is a plane ticket to Wailea-Makena?
In the last seven days, plane tickets to Wailea-Makena cost between and . Prices depend on a number of things, particularly the time of departure, carrier, cabin class and when the fare is booked.
Which airlines with flights to Wailea-Makena employ COVID-19 cleanliness policies?
While flying during the COVID-19 pandemic can be slightly overwhelming, airlines are doing all they can to protect the well-being of customers and crew. Here are a few carriers that have implemented changes:
  • Hawaiian Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.