Best Bookable Vacation Rentals in Hawaii

Are the white sand beaches, turquoise waters teeming with colorful wildlife, or the tropical tastes of Hawaii calling your name? Whether it’s a family vacation, group getaway, or romantic escape, these rentals all offer a private stay in some of the most idyllic locations across the islands. Click through for more and Happy Booking.

Feature image: Gather Vacations Rentals on Vrbo


Best Rentals Hawaii, Oahu, VRBO
Photo: Gather Vacations Rentals on Vrbo

Tucked away in the hillside of Lanikai, Hale Lani, which translates to “house in the heavens” in Hawaiian, lives up to its name. Perfect for families or groups, this secluded, two-story, three bedroom home easily sleeps six. Enjoy views of the famous Mokulua Islands and pristine Kailua and Lanikai shores from the wrap-around lanai (deck), or cool off in the private pool after a hike up to the nearby Lanikai pillbox. With a location just a 6 minute walk from the beach and a short drive to shopping, restaurants, and the farmer’s market in Kailua town, book your stay to relax and explore Oahu. 


Hawaii Rentals, Maui, VRBO
Photo: Hawaii Life Vacations on Vrbo

Papua Paradise, located on the West Coast of Maui, features panoramic views of the Pacific Ocean and neighboring Moloka’i and Lana’i islands. Soak up the sun at the pool featuring two wet bars or take a short walk to the beach where common green sea turtles sun themselves and colorful fish swim close to shore. This Hawaii pole-style, five-bedroom, private home comfortably hosts families and large groups. After a day of swimming, hiking, and exploring the restaurants and shops in nearby Kaanapali, sip a tropical drink on the Lanai as the sun sets over the ocean and freshly caught fish grills on the barbeque.


Hawaii Rentals, Kauai, VRBO
Photo: Ty and Ariana Owen on Vrbo

Minutes away from the popular South Shore town of Poipu, this 100-year-old plantation home is the perfect getaway for a family or group looking to experience the natural wonders of Kauai. Take a short drive to the nearby world-renowned beaches, shopping, restaurants, and breweries. After a long day of hiking, swimming, and snorkeling, end at the home’s private pool and walk through the gardens where avocado, banana, citrus trees, and fresh herbs grow.

Big Island

Vrbo Big Island Rental
Photo: Greg Erickson on Vrbo

Lounge on the covered lanai with your family and/or friends while overlooking a serene, manicured lawn, quiet sandy beach, and the beautiful blue Pacific ( watch for whales in the winter months). This oceanfront estate offers the perfect group getaway with a spacious indoor and outdoor area fit with dining tables for group meals and ample space to sit back, relax, and soak in the island’s natural beauty. Take a short drive to enjoy snorkeling at Paniau, a hike to ancient Hawaiian petroglyphs, or a whale-watching cruise from Puako Harbor. Nearby, Queens’ Marketplace beckons withshopping, dining, and weekly events like lei-making and hula dancing.

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Also please note that properties do change availability, so please check Vrbo website for latest information. 

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