Maui Luxury Vacation Rentals and Villas

Maui, often referred to as the “Valley Isle,” is a premier vacation destination known for its stunning natural beauty, diverse landscapes, and endless opportunities for adventure. Select a luxury vacation rental here and treat yourself to world-famous beaches, incredible whale watching during the winter months, a fantastic culinary scene and those gorgeous Haleakala sunrises and sunsets. From the lush rainforests and cascading waterfalls of Hana to the pristine beaches of Wailea and Kaanapali, Maui offers a unique blend of relaxation and excitement. Visitors can explore the dramatic volcanic landscapes of Haleakalā National Park, snorkel in the crystal-clear waters of Molokini Crater, or simply unwind on one of the island’s many world-renowned beaches. With its rich cultural heritage, vibrant dining scene, and luxurious accommodations, Maui promises an unforgettable experience for every traveler. Whether you’re seeking thrilling outdoor activities, serene spa retreats, or family-friendly fun, Maui has something for everyone, making it the perfect destination for your next tropical getaway. Browse Gather’s collection of Maui luxury vacation rentals below, and start planning your dream getaway.

Discover Popular Maui Destinations & Resorts

Welcome to the Valley Isle

Maui luxury vacation rentals span the island, offering a wide variety of choice to discerning travelers seeking that perfect hideaway that exudes both the comfort of a private home, but with the posh amenities so deserved when you finally take a break from your busy lifestyle. From chef’s kitchens to private lanais overlooking the Pacific, concierge service to arrange your family’s activities to infinity pools, these dream residences make every aspect of vacation a dream. 

In the former sugar plantation region of Kaanapali, today’s resort community invites savvy travelers who seek the finer things in life. With the West Maui Mountains as backdrop and panoramic views of Lanai and Molokai in the distance, this is the place for a truly elevated stay. Combining an undeniably traditional Hawaiian feel with modern amenities, Kaanapali vacation homes offer easy access to beaches, dining, shopping, water sports, island adventures and golf. Two of the best beaches on the island are right here, Kaanapali Beach and Kahekili Beach, separated by sacred Black Rock, where you can watch daring locals jump from the cliff into the aquamarine waters below. Stroll the beachfront path to Whaler’s Village, with its myriad restaurants and nightlife venues. Hop on a snorkeling excursion boat to Honolua Bay or Turtle Town. Or golf on two breathtaking Kaanapali courses or head slightly farther north to the two Kapalua courses. 

For unparalleled luxury, Kapalua luxury vacation rentals fit the bill. Not only will you find some of the island’s finest real estate here, but you’ll have access to the exclusive planned resort community’s award-winning dining, world-class shopping and excellent golf. Kapalua Bay Beach has been named the best in the world and has limitless water sports available. Follow the Kapalua Coastal Trail from here to tranquil Oneloa Beach and continue on to the Ritz-Carlton Kapalua’s D.T. Fleming Beach. Did we mention golf? It’s worth a second mention – the Plantation Course and the Bay Course have hosted numerous professional tournaments and will bewitch you with their beauty and challenges. 

In sun-drenched Kihei, Maui vacation rentals place you in a vibrant beach town with stunning views of the Molokini crater, the neighboring islands of Kahoolawe and Lanai and the West Maui Mountains. Beach lovers adore Sugar Beach and Keawakapu, two of the island’s longest beaches. 

For history buffs, a private vacation home rental in Lahaina takes you back in time. With overtones of the ancient Kingdom of Hawaii, yet decidedly 21st-century creature comforts, vacation homes in Lahaina are both storied and spectacular. Families love kid-friendly Kahekili Beach Park, snorkelers head to Black Rock and swimmers make for the calm waters of Kapalua Beach.  Some of the best whale-watching and sunset boat tours leave from Lahaina. 

Don’t overlook West Maui’s hidden treasure when selecting a Hawaii vacation home rental. This is where you’ll find Napili, a charming coastal community with lush vegetation and white-sand beaches. Life slows down here, giving you time to relax and recharge – but with the activities, dining and shopping of Kaanapali and Kapalua within easy reach when the mood strikes. 

Whether you’re traveling with friends, family or even pets, these private, luxurious rental homes in Maui have the upscale amenities you’re hoping for (WiFi, swimming pools, gourmet kitchens) with the comfortable feeling of home. Elevate your stay with private boat charters, guided whale-watching excursions, reservations at the hottest restaurants and most lavish spas – whatever you dream up can be arranged.