Road with Jacaranda tree blooming with purple flowers in Maui, Hawaii.

May Hot Picks: Where to Stay on Maui

May on Maui — is there anything sweeter? May is kicked off by Lei Day, a statewide celebration of making and giving lei, while fragrant purple jacarandas begin to bloom Upcountry. The temperatures haven’t reached their summertime peak, nor have the crowds. Below, we’ve uncovered some of the best deals and loveliest properties available for the month of May. Read on to discover our Hot Picks. 


Wailea Beach

South Maui: Kihei/Wailea

South Maui is known for fun and sun. This area receives less than 10 inches of rainfall annually, making beach days in South Maui possible almost every day. And with miles of golden beaches, it won’t be hard to find an ideal strip of sand to laze on. In addition to the wealth of ocean activities, one of South Maui‘s top attractions is Maui Brewing Company — the largest craft brewery in the state. Take a brewery tour, or sample Maui Brewing’s award-winning beers alongside dozens of other craft breweries at the Maui Brewers Festival, held every May at the Maui Arts and Cultural Center. The bi-annual Wailea Restaurant Week also takes place in May, making it an excellent month for foodies on Maui.  


Waiohuli Beach Hale B208 hot picksWaiohuli Beach B208

Looking for an affordable condo option on Maui? Check out Waiohuli Beach Hale B208! This charming 1-bedroom and 1-bathroom unit has been completely remodeled and features a loaded kitchen, Hawaiian-style furniture, and a King-sized bed with air conditioning. Don’t miss out on the beautiful courtyard, flower gardens, solar-heated pool, alongside the breathtaking views. Check your dates on Beach Breeze‘s Airbnb listing, but make sure to contact Martha directly in order to skip those commission fees that Airbnb charges you!




Pacific Shores A204 Hot PicksPacific Shores A-204

In Kihei, this spacious and tastefully decorated condo in South Maui is the perfect spot for your family vacation or getaway with friends. Pacific Shores A-204 has 2 bedrooms, 2 bathrooms, and room for up to 6 guests. This condo features a comfortable open floorplan, a balcony with a peek-a-boo ocean view, and access to a nice pool and hot tub area. Enjoy the convenience of being close to some of the best beaches, local restaurants, and shopping in Hawaii. Search your dates on the Airbnb listing, but book your stay directly with owner John Caubble via phone 808-280-3099 or email john@caubble.com!



The Palms at Wailea 1102The Palms at Wailea 1102

The Palms at Wailea 1102 is a private, 2-bedroom 2-bath condo with exceptional ocean views spanning from Makena to Kaanapali. You’ll enjoy ocean views from all rooms, with a large private lanai for discrete sunning, dining and relaxing. Toast the end of a perfect day with a panoramic Maui sunset from your private table on the lanai! Book directly with the owner for the best deal!




Hale Hui Kai 203

Experience comfort and convenience with a touch of island living at Hale Hui Kai 203. This newly-remodeled 2-bedroom, 2-bathroom condo features king-size beds, air conditioning throughout, and a fully-equipped kitchen with cookware, beach chairs, toys, towels, and more. Located steps away from Keawakapu Beach, and minutes away from golf courses, restaurants, and shops in Kihei and Wailea, Hale Hui Kai is the perfect spot for your island vacation getaway. Check your dates first and then book directly with Martha for the best deal (808) 283 2231!




Napili Bay

West Maui: Kaanapali/Napili/Kapalua

As the strong winter surf ceases and whales make their way back to Alaska, a plethora of ocean activities open up in West Maui in May. Ocean conditions allow for snorkeling almost every day, and parasailing and jet skiing are back on the table. Visiting on Mother’s Day? West Maui boasts an abundance of shopping, dining, and spa opportunities, making it ultra-easy to spoil mom. 


Kahana Manor 414 hot picksKahana Manor 414

Kahana Manor 414 is a newly-renovated and conveniently located condo in Kahana on the west side of Maui. This 1-bedroom, 1-bathroom condo has undergone a complete renovation and features brand-new appliances, AC units, and bedding. You will be just steps away from Kahana Beach and a short drive from Kapalua, Kaanapali, and Lahaina town from this condo. Plus, there are great restaurants and shops right below this unit, making it the perfect home base for your Maui adventure. Find your dates on the Airbnb listing, but book directly with property manager Scott Jordan at 808-283-0940 or reservations@mauiliferealty.com.




Hana Koki Beach

East Maui: Hana

As the COVID-19 pandemic has slowed and case counts have dropped below threatening levels, we are seeing more visitors traveling along the Road to Hana. This full-day excursion can be very taxing, and it is very hard to see all of what you want to see in just one day! The best way to experience Hana is to stop and stay at a condo or hotel in the area. Those are few and far between, but we have a great recommendation for you in May!


Hana Kai Oceanfront CondoHana Kai Maui

Hana Kai Maui features first-class studio, one- and two-bedroom condos set on exquisite oceanfront grounds. Many of Hana Kai Maui’s condos have panoramic oceanfront views allowing you to experience incredible sunrises and moonlit nights while turtles swim nearby in the surf. One-night stays are accepted in the ocean view and partial ocean view units (#101 – #205). Oceanfront units (#1 – #5) require a 2-night minimum stay (some exceptions apply). Book directly with the condominium for the best rate!



Whatever is drawing you to Maui this month, we hope you enjoy one of the loveliest months here on the Valley Isle! Happy vacationing!


  • Looking for great places to stay on Maui? You’ll save by BOOKING DIRECTLY with the owners/managers of these accommodations.
  • Looking for Maui deals? Sign up here for our free monthly Maui Deals & Steals enewsletter with the latest book-direct deals from our advertisers.  


Questions? Comments? Drop me a line: blog email

(Note: We recognize and respect the significance of the ‘okina and kahakō markings in the written Hawaiian language; however, we have omitted those diacritical markings on our site in order to integrate with the more common spellings used in online searches.)

©Copyright 2020 – Present, Maui Accommodations Guide. If you wish to share content from our site, you may do so only by publishing a link to our original content on MauiAccommodations.com, so full and clear credit is given to us. Any other unauthorized use and/or duplication of any materials on this site (either text or photos) without our express and written permission is strictly prohibited. For permission to use excerpts or photos from our site, please contact the publisher. Mahalo!

Maui Accommodations Guide © 2023 All Rights Reserved.