Fall is the Best Time To Visit and Buy a Vacation Rental Condo in Maui

Fall is the Best Time To Visit and Buy a Vacation Rental Condo in Maui

If you don’t mind missing out on the changing colors of the leaves, the temperatures starting to cool off, and don’t feel like flying to Europe for Octoberfest, why not make the trip to Maui this fall? Why? Because fall is the Best Time To Visit and Buy a Vacation Rental Condo in Maui. Fall is also one of the slowest seasons of travel here in the islands; this enables those who want to come to take advantage of both heavily discounted travel and lodging accommodations. This is great twofold because you can now invest more on your real estate with me!

Speaking of travel accommodations, be sure to check out our portfolio of fine vacation rental properties here in Maui.

*Make sure you read or at least scroll through the end of this post so you can see my wife, as Lady Spock and I in tight red running shorts!* Enjoy.

Sunset hike

Our leaves may not change colors, but our dreamy skies sure do. My wife Megan and I regularly enjoy this hike in the forests way above Ka’anapali

Are You FALLing in Love With Maui?

Because there are not as many visitors here on Maui, you are sure to experience smaller crowds at the airport and Costco. Many of the restaurants will be running specials. And best of all, many of the vacation rental condos that you want to invest in will not be heavily booked.

Helping buyer clients invest/sell vacation rental properties can be a tricky art to master. So, get into these high occupancy properties in order to truly understand what you are buying.

If you have several different properties you are interested in, we are only able to see them on back to back and check-in and check-out times. This can be very difficult to coordinate all while allowing you time to enjoy your vacation. However, during the fall, many of these are not as heavily booked. So it is much easier to coordinate showings for you.

Lastly, you will likely have less competition while you are property shopping due to less active buyers being on island.

We’ve Got Just the Place For You to Stay This Fall in Ka’anapali

Honua Kai Mahana Aerial

The Stice Team and Hawaii Life present our Ka’anapali, Maui Vacation Rental Portfolio

What’s Going on in Maui During the Fall Months?

Paddle For Life.

During the first week of this last October, my family and I paddled from Ka’anapali to Lanai to raise money for the Pacific Cancer Foundation. The 34-mile round trip journey was an incredible experience as we camped on the beach at Manele Bay. I had an amazing experience for this great cause.

The Maui Invitational Basketball Tournament is always a hit.

My cousin, Tim Stice, is a huge Oregon fan and we will be there to cheer them on. I used to sell fundraising tickets at the event as a young Boy Scout, to help raise money for our community. I have always enjoyed the energy here.

Maui Invitational


Halloween is one of our very favorite holidays to celebrate here in Maui. There is always quite the show on Front St. in Lahaina. This photo of us is from a couple of years ago when Halloween was not on a Monday like this year. So lame!

Be sure to check out some of the awesome keiki and adult activities here for the Mardi Gras of the Pacific event: Front St Halloween.


The Lower Kula Pumpkin Patch.

We highly recommend that you check out the huge pumpkin patch in lower Kula. Have a pumpkin carving contest like the Stice ‘Ohana did this last October. All the while sipping spiced pumpkin lattes and some awesome pumpkin grog for those of age.



As we reflect and give thanks for all of the love and goodness that surrounds us, the Stice ‘Ohana has enjoyed a long tradition of the laborious albeit quite enjoyable process of building the Polynesian underground oven, known as an imu. You can see Tracy and my dad, supervising on the far left of this photo, sharing his wisdom here on his craft: How to cook and prepare an imu Hawaii Life Style.

Imu Photo

Whale Watching.

We just had the first whale sighting on Maui a couple of weeks ago. So it’s time for all of us to honor and observe these amazing creatures. I recently found this video on Youtube and think it’s totally awesome. Video credit to Maui Whale Watching and their Youtube channel.

Festivals of Aloha.

Directly from their site, which runs throughout the state of Hawaii during the fall months:

“The mission of the Festivals of Aloha is to honor Native Hawaiian culture and traditions from generation to generation. This is to share them with visitors and people from the community. Our 2016 theme is “He Keiki Aloha, Na Mea Kanu” – Beloved children are the plants. Good farmers know that in order to grow truly healthy crops, plants must be cared for as if they are children. This reciprocal, familial kind of love is the philosophical foundation. It can fuel the soul of our people into an aloha-filled future.”

Screen Shot 2016-11-16 at 6.54.23 PM

The Hawai‘i Food & Wine Festival.

Directly from

“The Hawai‘i Food & Wine Festival, operating as a 501(c)3 non-profit organization, is the premier epicurean destination event in the Pacific. Set in the lush island paradise of Hawai‘i, the Festival will take place over three weekends on multiple islands. Featuring a roster of over 100 internationally-renowned master chefs, culinary personalities, and wine and spirit producers.

The Festival in Hawai‘i Island, Maui, and O‘ahu will showcase wine tastings, cooking demonstrations, one-of-a-kind excursions, and exclusive dining opportunities with dishes highlighting the state’s local farmers, fishermen, and ranchers.”

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This past September my wife and I attended our first ever HawaiiCon event at the Mauna Lani Hotel on Hawaii Island, which is a quick skip away from Maui. Yes, I know this is not a Maui event, but it was such a colorful event that I had to include it here. My wife is a total Trekkie and Battle Star Galactica fan. I was a bit out of my element as this isn’t really my thing, but we had a blast together.

Jeremy and Megan Hawaii Con

Doesn’t Megan make the most adorable Lady Spock?

Athletic Events.

If you enjoy running, I would highly recommend that you check out both the Maui Marathon and the Hana Relays, which run during the fall season of every year here.

Yes, that is me running 16 years ago at the 2000 Hawaii State Cross Country Championships of which our team very proudly took 2nd place

Maui Arts & Cultural Center Events.

Fiery sunsets, amazing talent, cool fresh breezes, beautiful sunny skies, and the occasional torrential rainstorm are all part of the agenda for concerts and events at the Maui Arts & Cultural Center in Kahului.

MACC Concert

My cousin Tim Stice, his wife Michaela Stice, myself, and my wife Megan

We always have a blast here and we are looking forward to supporting fellow Maui boys – The Walsh Brothers – in their highly anticipated big wave surf film, The Distance Between Dreams (below), and the Eric Church country concert coming up in early December. The MACC does a ton of events during the fall season so be sure to check out their full calendar for next year.

Let’s have the Maui boys show us how it’s done:

It’s time to FALL in love with Maui!

Jeremy Stice REALTOR (Broker #21286) Maui, Hawaii
Top 100 Realtor recipient in State of Hawaii (out of 14,000 Realtors) 2014, ’15, and ’16 
808.281.2178 Direct

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