Free Flights and 5 Nights at the Marriott Wailea Beach Resort Using Points


Hawaii is one of my favorite destinations and my favorite place to travel hack! We can’t seem to quit it and keep going back every year. We visited the Marriott Wailea Beach Resort, once in 2019 and then returned again in early 2020, before everything got wild. Both times we used points for all five of our nights and for both of our roundtrip flights! Here is how we did it this last time. 

Five Free Nights

We stayed at the Marriott Wailea Beach Resort. This resort is a category 7 property. The standard rate is 60,000 points a night, off-peak is 50,000 and on-peak is 70,000 a night. Your best bet is to go during off-peak times. To find those off-peak dates, you’ll want to search using flexible dates so you can see the price per night for a whole month. Being flexible can really help you save!

Note: Marriott has gotten rid of their award chart and moved to dynamic pricing. Award nights are now between 80,000-1000,000 points per night. 

To get the points my husband opened up the Amex Marriott Bonvoy Business card. When he signed up for the card there was a limited-time bonus of 100,000 points (the standard offer is 75,000 points). A few months later, Amex increased the bonus again. He referred me to his card and earned 20,000 points. I then earned 100,000 points by meeting the minimum spend of $5,000 in 3 months. One reason I love Marriott- when you book 4 nights on points, you get the 5th free! We were lucky to find 5 off-peak nights for a total of 200,000 points for our stay! It was super easy for me to call Marriott, transfer 80,000 of my points into my husband’s account, and then book.

Hotel and airline cards periodically increase their bonuses. As you can see, we like to take advantage of these opportunities! Make sure you are following us on Instagram and signup for our newsletter and we’ll keep you up to date on those increased limited-time offers. 


lobby of Marriott Wailea Beach

The lobby area. Beyond those palm trees, you can see the ocean.

One downside is that we did have to pay a daily resort fee and a daily parking fee. For the five days, this came out to be around $300 total. I feel like I can’t really complain about that though when the resort goes for over $500+ a night!

Free Flights

There are a lot of ways to fly to Hawaii using points. For our first trip to this resort, I transferred Chase Ultimate Rewards into my United Mileage Plus account. Each roundtrip flight was 45,000 points for a grand total of 90,000 points. Now, this isn’t the cheapest option out there but these tickets were the best option for our dates, had good flight times without super long layovers, and were super easy to book. I also have the United Explorer card which comes with two United Club lounges passes each year. We were able to spend our layover in San Francisco at the lounge, eating snacks and relaxing before our flight.

This last time in 2020, we booked our flights on Southwest. We found an amazing flight for 20,000 Rapid Rewards roundtrip per person! My husband has the Southwest Companion Pass, which allowed me to fly for free! Our total was 20,000 Rapid Rewards and about $23 in taxes and fees for both of our flights to Maui! 


Marriott Wailea Beach Resort

Now, let’s talk about the resort. When we arrived we were given fresh juice and leis, which always make you feel like you really are in Hawaii 🙂 We were also upgraded to a junior suite! The room was nice and spacious. It had a nice sitting area with a couch and tv and then around the corner was the bedroom with another tv and the bathroom.

The great thing about traveling to Hawaii is the time change. It is four hours earlier there for us so we woke up bright and early each day. I loved waking up each morning and walking through the beautiful outdoor lobby, seeing the ocean, hearing waves crashing, and the birds chirping. It was pretty empty this early and so peaceful.

Our morning routine was to wake up, grab some fresh fruit-infused water from one of the many water coolers, and go for a morning walk along the beach path. Along the way, we would stop, play a game of cornhole, and order a fresh acai bowl from a little food stand on the resort called Whale’s Tail. It was the perfect start to our mornings!



View from Marriott Wailea Beach Resort

More of the lobby area


Palm tree at Marriott Wailea Beach Resort



Tide pools Marriott Wailea Beach Resort

We spent a lot of time at the resort pools. There are three pool areas; one open to everyone, one for adults-only, and one geared towards kids. There are two infinity pools, one of which is the one for adults only. It was super nice but it was sometimes hard to find a seat there. The kid’s pool area was actually super fun. The reason being is the waterslides, of which there are four. Two of them are similar to what you would find at an actual water park! We weren’t the only adults who loved these slides 🙂

Girl sitting on beach chair at Marriott Wailea Beach Resort

These chairs were usually open and are just below the adults-only pool. They face the ocean and the view is gorgeous! It was a perfect spot to read a good book!


Waterslides at Marriott Wailea Beach Resort

These waterslides were fast and so fun!!


Infinity pool at Marriott Wailea Beach Resort

Just livin’ the life!


The resort location is fabulous! It is located along the beach with all the fancy hotels like The Grand Wailea, The Fairmont, and The Four Seasons. From the Marriott, it is just a short walk to Wailea Beach. At the beach, you’ll find hotel staff who will set up an umbrella and chairs for you to relax. It is first-come-first-serve but we always got there early enough to snag a seat. If you are looking to find turtles at the beach you won’t have to go too far! We planned to go snorkeling to find some but about ran into them right near the shore!

Mitch was surprised when he looked down and saw this sea turtle!


There are many other activities available at the resort. We loved the game room. Our favorite games were shuffleboard and double shot. We also enjoyed the fitness center. The equipment was really nice and new and the room was really spacious. There are restaurants right there on the property, but we didn’t eat at any other than Whale’s Tail and poolside service, the other places were pretty pricey.

Riding bikes at Marriott Wailea Beach Resort

Out on a fun little bike ride

Wailea is an expensive area, but the town of Kihei is just a couple of minutes away and you will find cheaper food options, grocery stores, and cheaper places to rent all your beach gear. When you go to Kihei, you have to eat at Coconuts! We actually went a few times. The food is delicious and the prices are great! We loved the fish tacos and the mahi-mahi plate with brown rice. Mmmmmmm, I could go for those fish tacos right about now!

Girl at Flemming's Beach in Maui

D.T. Fleming Beach


We’ve been twice already and can’t wait to go back. We would totally recommend this resort! It is a great place for families, couples, and everyone!


girl at Wailea Beach

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