Wailea-Makena Vacations from ￥76,423

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The Latest Wailea-Makena Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sands of Kahana

Sands of Kahana

3 out of 5
Price was ￥173,486, price is now ￥76,423 per person
￥76,423
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.2/10 Very Good! (446 reviews)
Staffs of front desk were so friendly and helpful.

Reviewed on Oct 12, 2025

Kahana Villa

Kahana Villa

3 out of 5
Price was ￥159,152, price is now ￥76,518 per person
￥76,518
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8/10 Very Good! (345 reviews)
Hot water ran out within 5 minutes besides that good hotel and location

Reviewed on Sep 30, 2025

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Price was ￥316,208, price is now ￥167,934 per person
￥167,934
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.6/10 Exceptional! (237 reviews)
We stayed in a renovated condo and it was beautiful. The grounds are beautiful with direct beach access. The pool was always crowded and it is small. No shade either. It also had direct access to the boardwalk to get to food and other options. Really quiet. The resort doesn't have a restaurant but that was fine for us. I would stay again.

Reviewed on Oct 16, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was ￥315,996, price is now ￥181,448 per person
￥181,448
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!

Reviewed on Aug 27, 2025

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

4.5 out of 5
South Kihei
Save 100% on your flight
Price was ￥320,924, price is now ￥184,866 per person
￥184,866
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
No reviews

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 ￥86,705 per night from Nov 13 to Nov 14
￥86,705
￥112,028 total
Nov 13 - Nov 14
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"Wonderful accommodations!"

Reviewed on Oct 10, 2025

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 ￥113,446 per night from Oct 30 to Oct 31
￥113,446
￥133,823 total
Oct 30 - Oct 31
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"I am not a big resort in Hawaii sort of person, but this was worth every penny and there were a lot of pennies involved"

Reviewed on Oct 10, 2025

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 ￥119,166 per night from Oct 18 to Oct 19
￥119,166
￥149,472 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Beautiful rooms and facilities, but not a lot of grab and go light dining options"

Reviewed on Oct 10, 2025

Fairmont Kea Lani Maui
See all 2,687 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 romantic area.

Kamaole Beach Park 3

What to do in Wailea-Makena

Best Ecotour on Oahu!

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

￥20,494
per adult
Bee Farm Ecotour and Honey Tasting in Waialua, North Shore Oahu
Waianae, Oahu: Swim with Dolphins

Waianae, Oahu: Swim with Dolphins (Semi-Private Boat Tour)

￥29,296
per adult
100% of travellers recommend
Waianae, Oahu: Swim with Dolphins (Semi-Private Boat Tour)
Famed North Shore Tour

Famed North Shore Tour

￥43,944
per adult
Famed North Shore Tour
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.