Wailea-Makena Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Wailea-Makena Vacation

Make organizing your next adventure a breeze with a Wailea-Makena vacation package. Whether it's the cuisine, nature or something else that draws you here, our packages will help you discover it all. Can't decide what should come first? Makena is one of the most popular cities to explore during your trip to Wailea-Makena. If you're ready to stop daydreaming and start doing, Expedia will help turn your Wailea-Makena vacation into a reality.

Top Wailea-Makena Vacation Deals

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

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was CA $2,925, price is now CA $2,129 per person
CA $2,129
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
8/10 Very good! (380 reviews)
The staff was very friendly and helpful. The room was not very clean.

Reviewed on Jul 21, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was CA $4,072, price is now CA $2,596 per person
CA $2,596
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (916 reviews)

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Price was CA $8,162, price is now CA $5,367 per person
CA $5,367
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
This is a super nice adult only hotel. Nice and quiet. Staff is wonderful. On point. Hotel car service is excellent with luxury cars available. The room is nice. Large and spacious. My only critique is that the restaurant has a limited menu. But selection is great. Highly recommend.

Reviewed on Jul 25, 2026

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
South Kihei
Price was CA $4,359, price is now CA $3,150 per person
CA $3,150
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
9/10 Wonderful! (1,010 reviews)
Fantastic stay will be coming back year after year

Reviewed on Jul 27, 2026

Ready to book your vacation to Wailea-Makena?

 

Choose your dates

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 CA $1,032 per night from Aug 27 to Aug 28
CA $1,032
CA $1,316 total
Aug 27 - Aug 28
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"The hotel amenities were nice; however, the hotel was not that clean. For two days, we saw the same dirty spot on the floor (it looked like a dried drink), and it wasn’t until the day before we departed that they finally mopped the floors. We also saw a few roaches inside the room. They told us that ..."

Reviewed on Jul 27, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,536 per night from Aug 18 to Aug 19
CA $1,536
CA $1,922 total
Aug 18 - Aug 19
includes taxes & fees
Fairmont Kea Lani Maui
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 CA $1,164 per night from Aug 23 to Aug 24
CA $1,164
CA $1,474 total
Aug 23 - Aug 24
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"Our stay was amazing. The staff and service were absolutely off the charts. The newly opened spa was the nicest I have ever been in. The food at the adult pool and service by the bar staff was impeccable. The main thing that stuck out to me was the genuine kindness and pride that the staff puts into ..."

Reviewed on Jul 22, 2026

Four Seasons Resort Maui at Wailea
See all 2,903 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Wailea-Makena attractions

A tropical beach with palm trees, a sandy shore, and the ocean.

Wailea Beach

9.4/10 (4,138 reviews)
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.
See properties

What to do in Wailea-Makena

Lahaina Sunset Dinner Cruise

Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta

CA $189
per adult
84% of travellers recommend
Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta
Maui Ocean Center All Day Admission Ticket

Maui Ocean Center All Day Admission Ticket

CA $79
per adult
90% of travellers recommend
Maui Ocean Center All Day Admission Ticket
Calypso Sunset Dinner Cruise

Sunset Dinner Cruise aboard Calypso: Prime Rib, Fish, Chicken or Pasta

CA $213
per adult
90% of travellers recommend
Sunset Dinner Cruise aboard Calypso: Prime Rib, Fish, Chicken or Pasta
See all activities in Wailea-Makena

Frequently asked questions

How much does a Wailea-Makena vacation package cost?
Get your credit card ready, because a trip to Wailea-Makena starts from only CA $2,129. When you combine your flights, hotels and more into a package, you'll land the best prices.
How do I get a cheap travel package to Wailea-Makena?
If you love bargains, bundle your bookings into a Wailea-Makena vacation package. Whether you're looking for flights, hotels, day tours or rental cars, you can book everything in one place. You'll have endless choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 properties all over the world to choose from. Fly with who you prefer, stay wherever you like and save your hard-earned money — now that's the ideal escape!
What are the top hotels in Wailea-Makena?
Maui Coast Hotel and Days Inn by Wyndham Maui Oceanfront are two great hotels in Makena. A must-visit on any good Wailea-Makena itinerary, we recommend taking the time to explore this happening city.
How far in advance should I book my Wailea-Makena vacation?
Browse Expedia to compare international airfares as soon as you know your travel dates. You can generally purchase a seat up to a year prior to departure. If it's too early for your preferred air carrier, or you're booking late, don't worry. Cheap tickets to Wailea-Makena sometimes appear just weeks before departure.
What does an Expedia Wailea-Makena travel package include?
Much of that depends on you. You can choose from a variety of Wailea-Makena bundles, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like activities and tours. Whatever your perfect Wailea-Makena break looks like, get set to save!
What should I know before booking a Wailea-Makena travel package?
A travel package can be easier on the credit card than individually booking all you need for your trip. For example, bundle your flights, hotels and rental cars and save big. Whatever sort of vacation you're planning, you're bound to find a package to suit your budget.
Can I choose my airline with a Wailea-Makena Expedia vacation package?
Yes, of course. Expedia has access to more than 550 airline partners throughout the world, so go with the carrier that's a good fit for your travel preferences.
If I'm not able to travel, can I cancel my Wailea-Makena vacation package?
Because we know life is full of surprises, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Explore a world of travel with Expedia

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