If you started your Maui planning on our home page, you have already determined when you are traveling and where you want your condominium to be. (Subscribe to download my Maui accommodations guide with links to my favorite properties on the island if you don’t know.) Now what?

Well, if you know which condo community or specific unit you want to stay in, the next step shouldn’t take too long. However, if you are more price sensitive and just want to find the best deal, be prepared to spend some time doing research on multiple websites and comparing all-in prices. Follow the tips below to secure the best rate on your next condominium vacation rental!

SECRET: If you don’t enter exact dates in your search, most booking sites will advertise the lowest rate the unit charges at any point during the year. These “From:” rates can be misleading. By adding just one discounted week to their calendar, property managers can make their high season base rate of $350 look like $175. Don’t fall in love with a unit out of your price range by always entering the dates you want to travel. High and low season prices in Maui can vary by hundreds of dollars. Also, always compare “all-in” pricing; not nightly rates. Condominiums have many one-time fees that may be added on, including cleaning, damage insurance, taxes, booking fees/commissions, etc. so you can’t do a true apples to apples comparison with nightly rates.

Always Book Owner Direct

Most people book condos and private homes through VRBO, Airbnb and property managers, but these methods all add booking fees to renters and take commissions from owners. Your best bet for getting the lowest rate is to book owner direct (remember lowest rate is the all-in price after fees, commissions, taxes, etc.).

SECRET: If you find a property you like on VRBO/Airbnb, do some internet research and see if you can find an owner direct website. Maui owners have to include their rental license on all listing sites, so if they’ve followed the rules, it is easy and you can just google their tax number.

Although it won’t be called by name, if you google our tax ID you can find Anthurium House on VRBO, third party booking sites and our on-island property manager’s website. You will always get a better rate here on Secrets of Maui!

Nervous about booking direct with an owner? Learn how to spot and avoid a scam with this article.

Fill Booking Calendar Gaps

To maximize profits, owners need to maximize their occupancy rates. If you find a unit you like with a hole in its calendar, consider contacting the owner and asking for a discount if you can fill it completely.

While it might sound like a good idea to try and do this with short stays in two different condo units (say 3 nights in one and 4 nights in another), be sure you factor in any fees they charge (cleaning, insurance, etc.) to calculate the all in price for both units.

Don’t Move

The longer you stay in a condo, the more affordable each night gets as you spread out the one-time costs over time. I only advise splitting locations for trips 10 days or longer. For shorter stays, you will waste valuable time and money by switching properties. Remember that there is usually a 4-5 hour window between check in and check out. What are you going to do with the food from your fridge? Where can you go where your luggage will be safe in the car?

Travel During Off-Season

Generally, the most affordable times to visit Maui are April and May before school is out and September through November when kids go back to school and the snowbirds haven’t arrived yet. The spring and fall “shoulder seasons” provide the fantastic tropical weather Maui is known for without the high rates and crowds that accompany the summer and winter. Deals are also easier to find for flights.

Search for Last Minute High Season Deals

In Maui, most popular condos are booked solid from Christmas until April months (and even a year) in advance. Discounts during high season are rare unless you are lucky and find a short gap between bookings or a hole caused by a last minute cancellation. Owners will typically advertise last minute specials on social media, so be sure to follow your favorite properties.