A hotel property might be the best choice for you if the thought of sipping a cold (but expensive) drink at a swim up bar is your version of heaven. If you plan to stay in a Maui hotel, you can combat high prices by trying these money-saving tricks. (Not sure if you are better off at a hotel or condo? Take this quiz!)

Off Season Travel

The cheapest time to book a hotel room in Maui is during the months of April and May before school is out and from September through November when kids go back to school and the snowbirds haven’t arrived yet. The spring and fall “shoulder seasons” still provide the beautiful tropical weather Maui is known for without the high rates and crowds that accompany high season.

Bundle

Booking your flight, rental car and hotel together can sometimes lead to savings. I prefer to book my items “a la carte” but this technique never hurts to try if you aren’t picky on brands. Most third party travel sites like Travelocity and Orbitz have this as an option. Always compare the bundled rate against your best a la carte combined pricing.

Last Minute Bookings

A hotel room’s price can fluctuate significantly, so always keep an eye out for price drops as your vacation date approaches. Travelers that don’t have a hotel preference can search for last minute deals in the weeks or months prior before travel. (I don’t recommend this method during high season!) If you choose this strategy, reduce your risk by booking a backup hotel room right away with flexible cancellation policies.

Travelzoo and Hotel Tonight are popular last minute travel search apps. Priceline.com and Kayak are two other options.

Price Alerts

If you don’t have time to track prices, sign up for alerts through websites like Hotels.com and Kayak. They’ll do the work for you and send emails when the prices start to drop.

The savings doesn’t have to stop once you’ve booked your hotel room. Yapta is a service that dynamically tracks prices on your hotel room (and booked airline tickets), sending instant savings alerts when prices drop. Tingo goes further and actually rebooks the room for you, crediting the difference back to your account. It also keeps an eye on other rooms in the same hotel.

Loyalty Programs

Hotel loyalty programs can save you money by offering free nights and upgrades, Wi-Fi access, exclusive events, etc. Marriott Rewards and Starwood Preferred Guest loyalty programs are fantastic if you remain brand loyal, sign up for and use their credit card, and travel frequently.

For those less brand loyal, consider third-party booking site programs. Hotels.com loyalty members can book 10 nights and get one for free. The ten nights can be mixed and matched in different locations.

Credit Card Perks

Most credit cards offer travelers a booking site where they can exchange points or miles for free or discounted nights. For example, the American Express Fine Hotels and Resorts booking tool gives room upgrades, resort credits, breakfast and offers a low price guarantee. (My credit card of choice, however, is through Alaska Airlines for their Famous Companion Fare program. We just booked our direct Alaska flights over Thanksgiving week for our family of four. Since my husband and I both have the card, the BOGO program just saved us over $2,000!)

Membership Discounts

Be sure to check for discounts with any professional organization, university or other group you belong to; you might be surprised at the offers you find! Discounts are usually available to members of AAA, AARP, ADP and the American Bar Association.

Final Thoughts

Aerial View of Ka'anapali Beach - Island of Maui - Hawaii

Book hotel direct or book third party? Unfortunately, you can’t be guaranteed which method is cheaper. The price will often be less on a hotel’s own website because, like booking condos owner direct, the hotel doesn’t have to pay any commission. However, you might be able to secure a lower rate through a third party website if they have prepaid room inventory and need to get rid of excess inventory. Utilize the websites mentioned above to find your best rate and then always compare it to the hotel’s website. If you find a better deal on a third party site, check to see if the hotel offers a “best rate match guarantee” by browsing their website or calling the front desk.

I always prefer booking direct if possible because you will have one less company to deal with if something goes wrong (like if they lost your booking; been there, done that!). Also, beware that booking with a third party may mean you don’t receive loyalty points from the hotel chain.