Maui

West Maui’s Top Luxury Vacation Rental Listings for Sale

If you are in the market for a higher-end vacation rental property for sale in West Maui, this post is perfect for you. These types of properties are excellent for 1031 Exchanges, or perhaps you are considering getting your “feet wet” to full-time ownership in Maui. These properties serve as perfect stepping stone to allow to you use them as much as you chose to while also having the luxury of renting them out for substantial revenue on a short-term basis. This post focuses on specific assets that are currently listed in the marketplace. If you are in the market for something like this, please reach out to me to be kept abreast of all opportunities on the open market as well as off market listings.

map of maui

I believe that all of the properties referenced below and in this series represent strong values at their respective price points. The majority of these properties don’t sit on the market long especially if they are priced appropriately as they represent unique values in our market considering that our regulations on short term rentals properties are very tight and I don’t think the County of Maui will be permitting any more construction of these types of properties.

If you are in the market for a more moderately priced vacation rental property here in Maui, please don’t hesitate to reach out- these assets typically start in the $500-600k range in today’s current market.

Kaanapali Shores 456 & 457 – Two Side by Side 3bd/2ba Residences

It’s rare that you see two properties located directly next to each other for sale- such is the case with these two fantastic offerings at one of my very favorite resorts in North Kaanapali: Kaanapali Shores Real Estate for Sale. These properties have the same physical layout where the primary bedroom lives on the ocean side of the first floor as well as the secondary bedroom, kitchen, and living area. The upstairs loft serves as the 3rd. bedroom area and a secondary den that would be perfect for an office or an additional play area for the kids.

Kaanapali Shores pool

Both Kaanapali Shores residences have a very similar strong ocean view from the living room area (photo above taken from lanai), master bedroom, and spacious covered lanai. All listing details for residence #457 can be found here listed at $2.7M and all listing details for #456 can be found here.

What I Love About These:

  1. Three bedroom vacation rentals at this price point are rare– there are many starting in the $5M range here on Maui in Wailea (Hoolei condos for sale and Wailea Beach Villas condos for sale), Kaanapali (Honua Kai condos for sale), and Kapalua (Montage Kapalua Residences for Sale) but not at this price level.
  2. There are two of them next to each other which means that you could occupy one while renting the other.  You could also potentially advertise these as a 6bd./4ba rental which is extremely uncommon and there is a strong demand for. I have done this for one of my vacation rental clients where we have a 3bd. residence and a 2 bedroom on the same floor of a condo in Honokowai and we advertise them together as a 5bd./4ba combined vacation rental experience- Nohonani 400/403 combo listing here. We rent this particular property out for more as a combined listing than if you were going to rent them independently due to the rare offering.
  3. Building sweat equity– both of these properties need a fair amount of work on the interiors to properly optimize them in my opinion. We just recently purchased an oceanfront 2 bedroom at the same resort that we are just about to complete our top to bottom remodel on as I am a very strong believer in the overall all value propositions and I see the same in these two properties.
  4.  Tremendous upside on the rental income. Currently, the rental numbers for this property extremely subpar due to a number of reasons which I won’t list here but would be happy to share in a private consultation but I do strongly believe in the upside as my team has taken over similar assets and more than doubled net revenue inside of one year.

Kaanapali Shores #456 Video Experience

Puamana 192-2 – Oceanfront Townhome in the Heart of Lahaina Town

Those who know Puamana know what a special complex this is- it truly is a massive 30-acre oceanfront park in the heart of Lahaina town that has a very residential feel to it (many people do live here full time as well) but does allow short term vacation rentals. This particular property is a direct oceanfront single-level 3bd./2ba fully remodeled vacation rental residence. All listing details can be found here on this incredible $4.3M property. 

oceanfront lanai at puamana townhome

What a cozy and incredible oceanfront experience from the oceanfront lanai of 192-2 at Puamana.

Why I Love This Property:

  1. It is completely turnkey and in excellent condition.
  2. The location can’t be beat- I have lived all over the island of Maui and there are truly very few places that are as special as Puamana- every time I drive the through the gates while gazing at the surf out front or the plumeria trees- a massive feeling of joy overwhelms me.
  3. Puamana vacation rentals do extremely well and I can’t think of a better home away from home. Our team is currently offering another 3bedroom direct oceanfront residence at Puamana that is one of the top performers in all of Hawaii Life Vacation Rentals- you can view residence 254-2 here and please don’t hesitate to reach out to me on how I think #192-2 would do in our top performing rental program.
  4. Puamana has epic summer time surf in front of it that is suitable for all ages and skill levels (depending on specific swell conditions) and has one of the raddest and most serene oceanfront pools that I have ever seen. This place radiates fun with kids rolling around on scooters and bikes, all ages out enjoying surfing, and beautiful tennis courts for those wanting to keep their skills sharp.

You can view all Puamana Real Estate for Sale here.

view from lanai

View from the very private lanai of Ritz #1226 looking down towards Flemming’s Beach and out towards Lipoa point where the World Class Honolua Bay lives.

Ritz Carlton Residence 1226 – Exclusive Oceanfront Living in Kapalua, Maui

Who doesn’t love the Ritz Carlton! I just recently toured this residence with a buyer client looking for a high end vacation rental property, we were all very impressed. The Ritz recently made upgrades on these rooms to include an oven and cooktop whereas before they did not have them and it was truly like a hotel room. The onsite Banyan Tree restaurant is one of my favorites in West Maui, we were just there the other night and I had an incredible island seafood curry that was exceptional.

Link to all listing details of this fantastic $3.75M residence here.

Why I Love This Property:

  1. This property is completely operated like a hotel meaning that owners really don’t have any involvement in the process and it is seamless as it can be.
  2. Shockingly strong vacation rental income- this property grossed over $70K for the month of July in 2022, reach out to me directly for the full financial analysis.
  3. Walking distance to Flemings Beach and the Kapalua Coastal trail- Kapalua is one of the best locations in Maui to keep active with its lower density and absolutely stunning lush surroundings and cooler temperatures.
  4. Extremely private and quiet location- this particular unit is located near the oceanfront of the building that faces directly out towards Molokai and Flemmings Beach- I love its privacy and serene nature.

View all Ritz Carlton Kapalua Listings Here for Sale

Ritz Carlton Kapalua Updated Owner Benefits

ritz carlton residence developer rental privileges

Montage Residence 1203 – Kapalua’s Preeminent Luxury Resort

Link to Montage Residence 1203 listing details here

kapalua bay

The Famed Kapalua Bay which the Montage and Coconut Grove condos for sale directly front. This is one of the most protected bays on the west side and is perfect for little ones and those looking to swim or snorkle in a very comfortable environment.

Why I Love This Property:

  1. I ranked the Montage as my personal #1 high-end vacation rental property in a blog post that I authored several years ago- Sapphires to Diamonds – Ranking Maui’s Top Luxury Vacation Rental Investment Properties
  2. Montage Residences have the highest average daily rental rate that I have seen in all of Maui and is one of the top rated destinations in all of Hawaii.
  3. Direct oceanfront location with views looking directly at the famed Kapalua Bay with year round sunsets. Many properties in Kapalua don’t get the best sunset exposure because they are located so far north but this particular home faces southwest which makes it ideal for those rare Greenflash sunsets that sometimes we get here in Maui.
  4. This particular residence is massive at almost 3,000 sq.ft. of interior living with a large lanai perfect for lounging and grilling on the high end bbq.

Check out Montage Kapalua Bay residences for sale here

If you will be seeking conventional financing on this acquisition, please note that the majority of these properties will require 30% down payment and many of them start to break even financially with 40-50% down, there can be exceptions especially if you chose to self manage the property which changes the equation drastically. Read more about this here in a previous post of mine- 3 Ways to Rent & Optimize Your Hawaii Vacation Rental Property

Work with a True Vacation Rental Specialist

  • Licensed since 2006 at age 23; Third Generation Realtor
  • Top Selling Broker in the Entire State of Hawaii age 40 or under.
  • $70M Sold in last two years and a very consistent track record of vacation rental condo sales.
  • Born and raised on Maui; Seabury Hall and Babson College educated.
  • Honua Kai and Kaanapali Shores Homeowner Investor and Ka’anapali Coffee Farm property owner.
  • Facts. Analysis. Performance.
  • Expert negotiator and astute contractual knowledge.
  • Comprehensive pricing Analysis- more valuable/insightful than an Appraisal.
  • Complimentary In-house design and staging services by Laura Lancaster of WIBU Interior Designs.
  • Commitment to stellar “white glove“ services.
  • Driven, Knowledgeable, assertive, determined, and fun to work with.
  • Solution-oriented and able to navigate very challenging issues.
  • Listens well and has strong communication skills.
  • Introduced and established Hawaii Life Real Estate Brokers, Hawaii’s Top Real Estate Firm to Maui in 2009.

My wife and I have owned an investment property at Honua Kai since 2014, we just purchased our second at Kaanapali Shores in 2023, I have represented countless buyers and sellers on Vacation Rental Properties in Hawaii, and we operate a top-performing vacation rental program operating within numerous resorts in Maui.

Jeremy Stice R(B) at Your Service

As the director of Hawaii Life’s West Maui Vacation Rental portfolio and one of Hawaii Life’s top-selling Brokers, my team and I are here at your service. I was born and raised here in Maui, am a third-generation Realtor, and my wife and I have called West Maui home since 2010-we enjoy sharing our passion for it with all who are interested. I make a commitment to pick up my cell phone as best as I can, return voicemails, text messages, and email in a timely fashion. I also work 7 days a week so feel free to call me anytime you need me. I am here at your service, I look forward to sharing my passion and expertise with you. Want to follow my blog via email updates? Please enter it below. This will not be used for any other reason than automatic blog updates that I post. Subscribe to the Jeremy Stice Blog Roll Here.

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