Vacation Rentals in Maui, Hawaii

Maui Beach Rental Guide

maui miami mapLooking for a great deal on a Maui beach house? Whether you’re booking a pet-friendly pool home in Lahaina, or a luxurious oceanfront resort condo in Kaanapali, you can easily snag up an affordable rate on Vacation Check out last minute deals, cancellation specials, unique offers, and even freebies (like a free golf cart or pool heating). Maui lodging deals are everywhere.

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The sprawling Haleakala National Park, the sparkling Hana Highway, the glowing, white sand beaches, the laid-back luaus – Maui beachfront vacation rentals are unsurprisingly tempting. Book an affordable oceanfront cottage on a secluded beach in South Maui, or luxurious vacation condo at a resort on the west side in Kaanapali. Whether your favorite scene is the beach, the golf course, the spa, the shops, or even underwater, vacation homes in Maui give you easy access to it all. Even if you’re on a budget!

Before browsing the 100+ Maui vacation rentals listed here, though, get the scoop on the climate, the geography, and the top activities and attractions on the island.

When to Book Maui Vacation Rentals

Thanks to the trade winds, you’re guaranteed flip flop weather all year long. For off season Maui lodging deals, and comfier weather, to boot, visit in the spring or fall. Whale watching, however, is popular in the winter, particularly February. Book way in advance or take advantage of a last minute Maui beach rental deals.

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  • Temperatures hover in the low 70s and mid 80s throughout the year, though they can creep up into the 90s in the summertime. West Maui is drier than the East, while the Upcountry is the coolest. Although the weather is always swim-worthy in Maui, if you hike to the peak of Haleakala, bundle up – temperatures can dip into the 40s!
  • Even if you book long-term lodging in Maui, it’s easy to pack: casual clothes, swimwear, and light jackets for the evening!

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Top Events

  • November through January: Holiday events all over Maui
  • February: Whale Watching
  • June: Maui Film Festival in Wailea, the Kapalua Wine and Food Festival in Kapalua
  • September: Taste of Lahaina in Lahaina
  • October: Front Street Halloween Celebration in Lahaina

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Where to Book Your Maui Accommodation

maui beach houseFrom luxury resort condos to long-term oceanfront villas, there are plenty of Maui vacation rentals to consider. But how can you choose your dream rental if you don’t know where to look? Here’s a guide to the island.

There’s a good chance you’ll fly into the Kahului Airport, located in the Upcountry. Thankfully, Maui is very tourist-friendly, and transportation from the airport ranges from shuttle to bus to rental car to taxi, so you’ll have no trouble arriving at your Maui beach house.

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South Maui

  • Kihei: A lot of ocean, a lot of wildlife, a lot of discovery, and a lot of relaxing – that’s Kihei. In South Maui, you miss out on a good chunk of the tourist pandemonium. In its place: six miles of beaches, endangered Hawaiian stilts, coots, and ducks, and the hawksbill turtle laying her legs on the shore (from July to December). Go for an underwater tour of coral reefs at Kalama Beach Park, or a drive along the dramatic Piilani Highway, or see how many local birds you can spot through binoculars at Kealia Pond. Book a budget-friendly Kihei beach home to keep the trip as relaxing as possible.
  • Wailea: Golf, spa, shop, and repeat. Wailea is all about the pampered life. Whether you’re practicing yoga poses at Wailea, Polo, or Ulua Beach, or your swing at Wailea Resort, you’ll definitely get that warm and fuzzy vacation feeling here. The Shops at Wailea are a scene stealer, cluttered with familiar and local spots, from Banana Republic to Ruth’s Christ Steakhouse to the Honolulu Coffee Company. Consider a luxurious, long-term Maui villa rental if you really want to get away.
  • Maalaea: Right on the bay, and great for snorkeling and sailing.
  • Makena: It’s easy to take it easy in this well-kept off Maalaea Bay.

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West Maui

  • maui horseback ridingLahaina: Formerly the capital of Hawaii, formerly whaling central… Lahaina on West Maui was formerly a lot of things. Sailors – including Moby Dick author Herman Melville – used to routinely anchor here, and King Kamehameha used to rule here. But what makes Lahaina beach condos so vacation-worthy isn’t just the history. If Melville were around today, he could still find inspiration for a Moby Dick spin-off or sequel on a whale watching tour from Lahaina Harbor or at the Whalers Village Museum. And modern-day tourists can balance out the history lessons with art galleries, fine restaurants, shops, golf courses, a visit to the Banyan Tree Park, and of course, the beach.
  • Kaanapali: The beach is front and center in Kaanapali, a straightforward resort town heaping with oceanfront condos, villas, cottages, and homes. In addition to the ocean, Kaanapali offers up a ton of tourist-friendly attractions – the Sugarcane Train is scenic and kid-friendly, the view from above is spectacular (try zip lining, parasailing or an air tour), and the quality golf courses are all over (the Royal Kaanapali Golf Course has hosted several tournaments). The biggest can’t-miss, however, is the local cliff diving ceremony. Every sunset, a cliff diver pays ode to King Kahekili by jumping off Black Rock. 
  • Kapalua: Focus on your golf game at the Plantation Course or the Bay Course, and then on relaxation in this nature-centric resort town. 
  • Napili
  • Honokowai
  • Kahana

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Maui Upcountry

  • Makawao: Where the Old West meets Hawaii. 
  • Paia: Bike around this adorable small town, hang out at Baldwin Beach Park, windsurf at Ho’okipa Beach Park, and kill time at the many local spas and shops. 
  • Haiku

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East Maui

  • Hana: Undeveloped and drenched in natural beauty. See it all on the Hana Highway, which zig zags around rainforests, waterfalls, and mountains.  Also make sure to stop by the Hasegawa General Store, full of intriguing items that put cheesy souvenirs to shame. Beachfront condos in Maui don’t get much more remote than this!

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Central Maui

  • Wailuku: Look forward to a variety of adventure here, like hiking the Iao Needle State Monument, riding horseback at Makani Olu Ranch, and finding one-of-a-kind items on Market Street.

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More Maui Vacation Guides

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