Distinctive luxury properties for the ultimate trip
Distinctive luxury properties for the ultimate trip
Start-to-finish trip planning
Concierge teams coordinate your arrival, departure, and everything in between.
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Every Luxury Retreats home is personally verified to be in pristine condition.
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Premium, on-demand assistance for any question, at any time of day.
91 luxury villas and vacation rentals in Maui County
1 – 16 of 91 Rentals
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Maui vacations - a world away from the norm
A day in Maui starts like this: a long drawn-out breakfast on your oceanfront lanai, with fresh pineapple from the island and a cup of world-famous Kona coffee. Next up is a stroll along the beach, or a swim in the ocean. Or both. Then simply rinse and repeat, for Maui is an island to enjoy at your leisure.
Of course, some travelers live to get their adrenaline pumping - and there’s no better way to do it than hitting the surf. No matter if you’re an absolute beginner or an experienced rider, there’s a break with your name on it here. If you’re surfing for the very first time we recommend booking a few lessons to get you started off - and the Luxury Retreats concierge team can organize it for you. Beginners should be looking for a long-breaking, gentle wave such as those found on the south of the island, like Launiupoko beach. If you already know what you’re doing then head to the north shore - breaks such as Hookipa and Honolua Bay are sure to challenge you - but be warned, they can be tough to handle. If this all sounds too much like hard work, the simply pick a spot on the sand and watch the masters at work - surfing is a spectator sport after all.
Drive the road to Hana
Give all five senses a workout on the spectacular Road to Hana. A bucket-list item for many travelers, this twisting turning highway takes you through lush forests, with waterfalls breaking just off the tarmac and incredible views over unspoiled beaches. You’ll need to make an early start to get the most out of the trip, and bring plenty of provisions with you - food options are quite limited along the road. With over 600 hairpin bends along the route, if you’re not super comfortable behind the wheel you might prefer to take part in a guided tour. Your guide will offer plenty of places to stop along the way for photo ops. Once you reach the charming town of Hana, you can wander around or lace up your boots for the ½-mile trek to the Pools of Oheo for a refreshing swim. If you do drive yourself, make sure you set off home again by 3pm so you can navigate the return journey before it gets dark.
Head to the beach
With over 30 miles of beaches on the island, choosing which one to try on any given day can be a challenge. It’s good to remember that the waves can be very strong in Hawaii (remember, it’s a surfing paradise), so if you’re looking for a beach where you can swim, or where the kids can play, choose one with calmer waters. The best options include Makena beach - a beautiful stretch of sand with gentle waves on the south side of the island - and both Kaanapali and Wailea beaches, which have lifeguard patrols and regular beach amenities. Our Wailea beach villas are the ideal choice if you’re considering a beach vacation with family in tow.
Hike to your heart’s content
Avid hikers will love the wealth of challenging trails on Maui. For an easy way to enjoy the island head to Waianapanapa State Park, where a mostly level trail heads to a black sand beach with natural lava tube that you can explore. For a truly memorable day, make the journey to the stunning summit of Haleakala mountain for a hike that will take you above the clouds. Many visitors flock here to watch the incredible sunrise, but there’s more to explore than a photo opportunity. A guide will take you through the challenging terrain of Waikamoi preserve, where you’ll spot rare birds and other wildlife and enjoy incredible views. The weather changes very quickly up on Haleakala so make sure you come prepared with proper boots and rain gear.
Experience the luxury of our Maui vacation rentals
Maui is all about laid-back living, the true spirit of Aloha. That’s why our luxury rentals come equipped with backyard BBQs, swimming pools and shaded lounge areas made for relaxing with friends and family.
Wailea beach villas
For a vacation with the beach right on your doorstep, look no further than our beach villas in Wailea. Many of these luxurious properties have access to shared resorts amenities, such as a swimming pools, fitness centers and golf and tennis court access. Our concierge team can arrange all sort of little extras, like in-villa massages or yoga classes, and you’ll love the spacious outdoor dining areas. If you’re visiting the island in winter or spring, you might even spot a pod of whales on their annual migration while you’re relaxing on your lanai.
Lahaina vacation rentals
Nestled between the ocean and the mountains, Lahaina is a charming community with a bustling main street. Our Lahaina vacation rentals are perfectly positioned for you to take advantage of everything Maui has to offer - great coffee in town, challenging hikes in the mountains and refreshing swims from the beach. What’s more they boast spacious outdoor areas, swimming pools and amazing views at every turn. Music fans should make a beeline for Fleetwood’s on Front St, where Fleetwood Mac frontman and Maui resident Mick Fleetwood often performs live with local musicians.
Watching the sunset is a favorite pastime on Maui, and our Kapalua villas are in one of the hottest spots on the island for enjoying the nightly sunset show. The key ingredients for this ritual are a spacious lanai, a cold beer, and being surrounded by your favorite people. At our properties in Kapalua you’ll have all this and more. Many of the properties offer access to resort amenities such as pools and spa treatments. What’s more our Kapalua homes are just minutes away from some of the best beaches and golf clubs on the island. If you have kids, look out for a property on a resort with organized children’s activities - the kids will love it, and you’ll love a little bit of peace and quiet too!