Updated: June 2022
This post has been updated to include a roundup of my favorite boutique properties and vacation rentals in Maui.
Ever dreamt of having a tropical hideaway where you can wake up every morning to a sweeping view of the Pacific Ocean? It is time to make Maui your home away from home.
Maui is the perfect island when you’re looking for a laidback escape where you can unwind and live like the beach bum you know you were always destined to be. And if you’re island hopping or haven’t decided which island is right for you, check out the coolest Airbnbs on the other Hawaiian islands here!
Ready to grab those flip flops and fly away? Here are the coolest Airbnbs in Maui to stay on your next Hawaiian adventure.
When you want to get away from it all (but still have restaurants and shops right outside of your door), it’s all about this romantic hideaway nestled in an organic nursery.
Fun fact: This is actually the very spot where Jimi Hendrix stayed when he was in town filming the flick Rainbow Bridge. So, lie back, pop in this movie, and imagine coming back home here after a long day as a rock god.
With all of the comforts of home along with the convenient amenities of a hotel, this is the perfect place for your crew to retreat to. This well-appointed property can comfortably house up to six guests.
I absolutely adore the idea of renting a big house like this so everything one can stay together rather than being scattered across a hotel. Oh, and the 50-foot lap pool and hot tub are pretty nice perks too!
This Asian-inspired hideaway truly showcases all of the best that Hawaii has to offer. Located on a twenty-acre coffee plantation, you’ll have jaw-dropping views of the ocean, tropical jungles, and the mountains beyond.
Insider Tip: I’d highly recommend asking the owners for a tour of the grounds. They’re happy to walk you around the plantation and take you up to a tucked-away spot with ancient Hawaiian pictographs.
Been dreaming of the van life?
This cool accommodation option will let you travel around in style in a camper van. And, trust me, this is no old-school camping trip. With a modern kitchen and bathroom, along with a cozy lounge space, this upgraded RV is anything but roughing it.
Lounge in the saltwater hot tub for a romantic night in, then get up bright and early to hit the beach. From boogie boards to snorkel gear to beach umbrellas, this Airbnb has all of those little features that make traveling feel oh-so-easy.
This two-acre property in Maui’s North Shore is an ideal base for exploring the postcard-perfect beaches and hiking trails. Spacious enough for four people, this comfy cottage has all of the little touches that will make you feel right at home.
I love the laid-back vibe of this luxury two-bedroom townhouse. When you check into this breezy cottage, you’ll find a private tropical garden with a striking view of the mountains that is perfect for relaxing after a long day out.
With tropical hardwood floors and a vintage Hawaiian vibe, this cool one-bedroom bungalow will make you feel like a retro tourist living it up on an exotic expedition.
This comfortable and modern two-bedroom apartment can accommodate up to six people comfortably. Have a barbecue on your private patio then go downstairs for a swim and a long lounge in the sun.
This cozy Cove Beach village has room for four, plus a primo sun-drenched patio. Soak in the rays, go for a swim, then decide if you even feel like leaving the villa today.
This surf-inspired two-bedroom spot is perfect for up to four guests craving that beach vibe. The lovely loft is equipped with everything from a vinyl record player to ukuleles.
You’ll also find handy amenities like yoga mats and a shared space with a BBQ, pool, and hot tub. Oh, and be sure to sample that in-house Hawaiian coffee.
Just outside of Haleakala National Park, you can sleep under the stars with a sweeping view of Maui’s Central Valley and the coastline.
It’s perfect for a romantic night of stargazing. Plus, as a major perk, there is a normal fully indoor bedroom available in the main house too so you can tuck in if you get chilly or just want to get your feet on solid ground.
Located in the historic Wailuku Town, a two-bedroom villa is definitely one of those places that will make you feel like a local. Play house in Hawaii with up to six of your fave people while you explore the local food trucks, shops, and other top-notch hangouts.
This retro log cabin from the 1920s is a world away from the lines of hotels in the tourist districts. If coming home after a long day of exploring to curl up in front of the fireplace with a warm cup of tea sounds good to you, sign up here.
This two-bedroom cottage is perfect for an extended double date or families looking for a tropical treat. Right on the beach with a wrap-around deck, this place instantly feels like a home away from home.
A bonus perk: All of the cottages at Popolana are dog friendly so it brings Fido along with a swim session.
Nestled in a lush garden of fruit trees and tropical flowers, this cozy one-bedroom spot is perfect for a romantic escape. Watching the sunset from the sofa, this is a perfect place to unplug and get in some good old fashion quality time together.
Island hopping? Be sure to check out the full rundown of the Coolest Airbnbs in Hawaii.