Hawai’i Vacation Rentals and Villas

Our luxury Hawaii vacation rentals span the islands – from Oahu, Maui, Kauai and the Big Island – giving you ample choices on where to go and what vibe you’d like your getaway to have. Choose Oahu for bustling Honolulu and legendary surf towns like Haleiwa. Maui is always marvelous, thanks to its famous beaches and Haleakala peak. The Island of Hawaii, or the Big Island, woos visitors with its rich history, active volcanoes and coffee plantations. Kauai is draped in lush, emerald valleys and mountains, and known, quite rightly as “The Garden Isle.” Enter dates below to browse all of our luxury Hawaii rentals, or choose your desired Hawaiian island and then start your search. We look forward to welcoming you to our beautiful properties across the Hawaiian islands! 

Discover Gather Vacation Rentals on these Islands

Welcome to Hawai’i

Palm trees swaying on a light tropical trade wind, sugar-fine white-sand beaches, massages in beachside open-air pavilions, casual beach bars where you can sip a cocktail with your toes in the sand, epic golf, snorkeling with sea turtles … you get the picture. This island reverie becomes a stunning reality for those vacationing in Hawaii. With its warm aloha spirit, glimmering ocean, bubbling volcanoes and emerald valleys, plus its fair share of super luxurious vacation rental homes, the islands are an easily accessible, technicolor dream come true.

Hawaii luxury vacation rentals span the islands – from Oahu and Maui, Kauai and the Big Island – giving you ample choices on where to go and what vibe you’d like your getaway to have. Choose Oahu for bustline Honolulu and legendary surf towns like Haleiwa. Maui is always marvelous, thanks to its famous beaches and Haleakala peak. The Island of Hawaii, or the Big Island, woos visitors with its rich history, active volcanoes and coffee plantations. Kauai is draped in lush, emerald valleys and mountains, and known, quite rightly as “The Garden Isle.”

Oahu

Choose a private vacation home in Oahu for easy access to authentic Hawaiian experiences. Feel the pulse of modern life, as well as the values and traditions of the Hawaii of yesteryear. Oahu’s various regions provide an array of Hawaii vacation rental choices, from posh Diamond Head with its SoCal verve to quieter Hawaii Kai on Hanauma Bay.  For a similar residential vibe, check out Aina Haina, a family favorite for its proximity to outdoor activities and a blend of sall community and city personalities. Choose an exclusive vacation home in captivating Kailu for its top beaches or the planned neighborhood of Lanikai, from which you can easily kayak over to the two Mokulua islands. On the boho-chic North Shore, step out from your luxury rental home to check out the big waves in the winter or the calm, swimmable waters of the summer. 

Maui

Home to Hawaii’s Iao Valley, Maui is a perennial favorite for those seeking a Hawaii luxury vacation home in which to recharge and reconnect. Treat yourself to world-famous beaches, incredible whale watching during the winter months, a fantastic culinary scene and gorgeous Haleakala sunrises and sunsets. The resort community of Kaanapali invites savvy travelers who seek the finer things in life to soak up its undeniably traditional Hawaiian feel combined with modern amenities, easy access to beaches, dining, shopping, water sports, island adventures and golf. 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. 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. And, 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. 

Kauai

With timeless appeal, Kauai offers luxury vacation homes for every group and interest, inviting guests to get out and explore the allure of the island. Reminiscent of old Hawaii, Hanalei in North Kauai offers vacation rental homes in the gorgeous region of Haena, where countless Hollywood film crews have sought out the lush, untouched beauty of this area for their scenes. Choose a Kauai luxury vacation home on the Coconut Coast in the largest town on the island, Kapaa. For those seeing stunning Hawaiian scenery but who also want shopping, dining and plentiful activities, this is the perfect selection. 

The Big Island

 The Island of Hawaii is the youngest and largest of the archipelago. When you choose an exclusive vacation home rental on the Big Island, you’re not hemmed in by any one Hawaiian experience; instead, you can travel through numerous climate zones, from west tropical to polar tundra, in one day. From the jet-black sands of Punaluu Beach to the geologic wonders of Hawaii Volcanoes National Park, a Big Island vacation will humble and awe you. Historic Hilo offers vacation rental homes in one of the lushest places in Hawaii. Savvy guests come here time and time again for the city’s historical storefront, flourishing downtown, restaurants, art galleries and outdoor appeal. Nearby, vacation rental homes along the Hamakua Coast are opportune for those seeking relaxation or to take day trips within the island, including the Waipio Valley, Laupahoehoe Point and Akaka Falls. The Kona Coast is a vacationer’s paradise with exclusive vacation rentals perfect for honeymooners and families, where it’s easy to both hide away and to venture out into the wider coastal area. For foodies, Kailua-Kona luxury vacation homes place you within striking distance of eateries focused on farm-to-table local fare, craft beers, local Kona coffee shops and more. Mauna Kea vacation homes allow access to all the amenities of the Mauna Kea Beach Hotel and Hapuna Beach Prince hotel, while surrounding yourself in the luxuries and comforts of a private residence. For those seeking a sleepy Hawaiian hamlet, choose a Big Island vacation rental home in Puako, a sleepy hamlet on the Kohala Coast. Known for its exceptional beaches – and the luxury vacation rentals and residences that sit along the oceanfront – the area is home to crystal-clear water, the most extensive petroglyph fields in Hawaii, year-round sunny skies and spectacular sunsets.