Top 10 Maui Luxury Vacation Rentals

When only the best on Maui will do, book directly with the Property Manager for each of the Top 10 Maui luxury vacation rentals. Only the best will be listed on our Maui luxury vacation rentals list, from Maui luxury homes to vacation rentals featured in your favorite blockbuster movies. Book directly with the Property Manager for each Maui luxury vacation home. Our list is compiled from our experience staying at many of these Maui luxury vacation homes. For over 20 years we have been in the Maui luxury vacation rental business. When you’re ready for your next Maui vacation take a minute to look at the best luxury vacation rental homes and what they have to offer. Stay where the elites have stayed, from the Obama luxury home to Maui rentals featured in your favorite blockbuster movies. Our list covers it all.

All about Maui

The incredible Island of Maui (also known as the Valley Isle or the Magic Island) has become THE hot spot for many travelers in the know. The Island affords visitors the ability to both find a beach that only has you on it as well as return to civilization and enjoy first-class comforts, amazing food, and culture. Our list of Maui luxury vacation rentals covers the most popular Maui Cities.

Experience Hana

An essential part of the Maui experience is making the drive out to Hana. Some of the most incredible scenery on the planet awaits you. You will drive through rainforest and desert, pass over more than 50 one-lane bridges and see more waterfalls in a few hours than most see in a lifetime. Go slowly and stop at the various roadside stands to buy delicious banana bread, coffee, and local fruit. Just before the town of Hana, check out Waianapanapa State Park. The park boasts a black sand beach, a lava arch, and several freshwater caves (super chilly).

The historic town of Hana is rich in history, beauty, and culture. Go slow here too and talk to the locals to find out what appeals most to you. The hard-to-find Red Sand beach tucked behind the Hana Harbor is a favorite of locals and provides visitors with an incredible photo opportunity.  The beaches of Koki and Hamoa are also in Hana and can frequently have good surfing and bodyboarding. The town also has the luxury hotel Travaasa, the Hasegawa General Store (famous for having one of everything), and the Hana Ranch Store and Restaurant. The town also boasts a myriad of lunch trucks with the orange Surfing Burro being the most famous. The fish burrito is ono (delicious in Hawaiian).

Intrepid souls can opt to complete the loop back around the island (rather than returning the way they came) and pass by the Olivine Pools, Seven Sacred Pools, incredible waterfalls, the gravesite of Charles Lindbergh, super-narrow passes and bridges, desert-like vistas and cross through many unpaved sections of road. You will end up in Ulupalakua where you can enjoy a well-deserved glass of wine at the Maui Wine vineyard and hope to catch the sunset.

Upcountry Maui

Upcountry on Maui is rarely visited by first-time travelers to the island but is often found and treasured by repeat visitors. Cooler weather than down by the beach, shocking purple Jacaranda trees, and incredible protea flower farms await those that make the journey. Watching the sunrise from the top of Haleakala is a big draw (you need to make reservations to get into the park), grabbing breakfast at Grandma’s coffee shop in Keokea, wandering through the grounds of the Lavender farm, enjoying the incredible view from Rice Park and the Kula Lodge are all to be found here.

The Haliimaile General store restaurant is in the historical pineapple town of Haliimaile and boasts several awards for its Hawaiian fusion cuisine.  Haliimaile is growing as they now have a distillery making Pau Vodka and Paniolo Whiskey as well as a Glass Blowing shop.

Makawao is a must see

The cowboy town of Makawao is great for window shopping at places like Pink By Nature, Driftwood, and The Dragon’s Den.  The town also has several art galleries and quality eateries like Polli’s Mexican Restaurant, Casanova Italian Restaurant, Freshies Maui, Habibi on Maui, The Stopwatch Cafe, Kojima’s Sushi, and Kamado Bakery,  as well as a great yoga studio.

Kihei beaches are peaceful

Enjoy the vibrant town of Kihei and discover restaurants (Cafe O Lei, Three’s, Nalu’s, Lavarock, Miso Phat, 808 Deli, Paia Fish Market South Side, Eskimo Candy, Fabiano’s, Moose’s, etc ) bars, coffee shops, and art galleries as well as beginner surfing at Charley Young beach park or just cruise at the Kamaole Beaches.

Mulligans on the Blue is a favorite local and tourist watering hole that often has great live music at night.  If you are lucky the legendary Maui guitarist virtuoso and performer Willie K will be in the house.

Shopping at Wailea

Visit Makena and Wailea in the shadow of the mighty Haleakala volcano and enjoy unparalleled beaches (Big Beach, La Perouse, Keawakapu, Polo Beach, etc.) and incredible views of the offshore islands of Molokini, Lanai, and Koholawae.  Wailea has some of the best golfing in the world (Wailea Blue course and the Emerald Golf Course) as well as high-end shopping (at the Shops of Wailea) and arguably the most luxurious resorts on the island (Grand Wailea, Four Seasons, Andaz, Fairmont Kea Lani, Hotel Wailea, Makena Surf Resort, Ho’olei, etc.).

Finest surfing

When heading out to the west side you will need to pass through the towns of Maalaea and Olowalu. Maalaea is a small harbor town from which many snorkel, dive, whale watching, and fishing tours depart from. It is also home to the Maui Ocean Center (a great choice for kids or the rare rainy day on Maui) as well as some fun restaurants (Beach Bums BBQ & Grill, Seascape, Tante’s Fishmarket, Thai Paradise, Tradewinds Deli, etc.). One of the most challenging surf breaks on the Island, called Freight Trains (a running right-hander), is also in Maalaea. It rarely breaks but when the perfect south swell hits the island, it’s well worth checking out.

Cell service is optional

The town of Olowalu sits between Maalaea and Lahaina and is one of the lesser developed areas of the island, a sort of in-between destination. Cell coverage here is weak but the food is strong. Leoda’s Kitchen and Pie shop is one, if not the best lunch spot on Maui with incredible sandwiches and of course pie. The General Store has lots of last-minute items you might want for the beach as well as yummy shave ice. Make sure when looking at Maui luxury vacation homes in this area you have cell service.

Historic Lahaina

On the West Side the historical whaling town of Lahaina, which served as the first capital of Hawaii, now has a vibrant surf scene (Lahaina Harbor, Shark Pit, Breakwall, Puamana Pools) as well as great food (Fleetwoods, Prison Street Pizza, Pioneer Inn Grill and Bar, Cool Cat cafe, etc.) and art galleries (Wyland, KaiNani, Sargent’s, Harte, Lahaina Galleries, etc.). 

A walk around town will lead you to the massive Banyan tree park (which often has arts and crafts for sale beneath the huge branches). Make sure not to miss checking out the partial reconstruction of the Lahaina fort (originally built in 1831), the old Lahaina Prison (built-in 1852) as well as some other historical buildings like the Courthouse and Baldwin house that have been preserved over the years. Many of the snorkeling and fishing tours as well as ferries to the islands of Lanai and Molokai leave out of Lahaina harbor. A hidden gem in Lahaina is the Star Noodle restaurant serving up incredible dishes like Steam Pork Buns, Garlic Noodles, Pad Tai, etc.).

Past Lahaina you will come into the resort towns of Kaanapali, Kahana, Napili and Kapalua.

The sugar train is in Kaanapali and the visitors’ center is a fun way for kids (and adults!) to envision the past days when sugar and pineapple dominated the economy of the island. The train infrequently runs, so call ahead to see if you can get a ride or just visit the welcome center.

The West Side resorts (Westin, Aston, Marriott, Royal Lahaina, Alii, Honua Kai, The Whaler, Eldorado etc.) can be a fun way to break up your day, enjoy the pool and or spa, great restaurants, and shopping (especially at the Whaler’s village).

Walk the beach in Kaanapali

Kaanapali also has a great beach walking trail that takes you through the heart of the action. Many restaurants and bars have live music and views of the ocean. From the south end where the Hyatt’s Drums of the Pacific Polynesian Luau lives to the north end where you can find the Black Rock snorkeling and cliff diving area, you could spend an entire vacation just hanging out on this stretch of beach.

The Maui Brewing Company is in Kahana and offers a wonderful selection of local beers.  Freda’s overlooks the old Mala Wharf and has incredible Mexican food and an oceanfront dining experience. Ask your property manager when looking at Maui luxury vacation homes, often times they can slip a case of local beers to sip on after your journey to Maui.

The beaches of D.T. Flemming and Honolua Bay are not to be missed. Honolua has some of the best surfing in the world with the women’s world surfing championships usually being decided here at the end of each season. The Bay also has great snorkeling on the inside when the swell isn’t pumping.

Maui luxury Resorts abound

The Resort town of Kapalua has several resorts (Montage, Ritz-Carlton, Kapalua Villas, Alii, etc) as well as great golfing (Plantation Course and Bay Course). The Montage also has the unique Cliff House venue which frequently hosts champagne events in a one-of-a-kind oceanfront setting. Often times our Maui luxury vacation homes have many of the same perks as these resorts.

On the North Shore of the island, is the town of Paia with its laid-back hippie, surfer vibe. The town is easy to walk and has many great restaurants (Charleys, Paia Fish Market, Cafe Mambo, Cafe Des Amis, Rock & Brews, FlatBread, Milagro’s,  etc.), art galleries (Art Project Paia, Cesere Brothers, Studio 22K, Indigo Paia etc.) as well as Baldwin and Paia Bay beach parks.

Windsurfing and Honu

Just down the road past Mama’s Fish House, is Hookipa Bay which has great surfing and windsurfing. The Bay also frequently has turtles basking in the sun on the beach allowing visitors a rare opportunity to see the ancient and majestic creatures up close.