12 Best Vacation Rentals in Hawaii
Sunny Escape: Poipu, Kauai
From $295 per night; vrbo.com
When staying here, we’re not sure what would cause us to smile more: Setting out on foot for a day at Kauai’s stunning Poipu Beach (just a short walk away!) or returning home to this sunshine-yellow retreat along a quiet street. The historic plantation-style home is just over 1,000 square feet and lovingly restored. We’re crushing on the high ceilings, beautiful chef’s kitchen, and screened-in lanai.
Aloha Spirit: Haiku, Maui
From $499 per night; Boutique-Homes.com
We couldn’t picture this plantation-style home anywhere else but on the shores of Hawaii. The five-bedroom beauty exudes island charm inside and out, from the tropical-inspired interiors (we’re dying over that turquoise bedroom!) to the foliage that surrounds it. If nothing else, you’ll leave Hawaii with a healthy dose of decorating inspiration – and a desire to come back really soon.
High Style: Fern Forest, Hawai’i
From $200 per night; Airbnb.com
If the bustling side of the Big Island isn’t your thing, this off-the-grid hideaway is the perfect escape. Tucked 50 yards back into a tropical jungle, the tiny, solar-powered treehouse is glamping at its best, with a fully enclosed living space with floor-to-ceiling windows, an indoor-outdoor shower, hanging daybed, and wraparound lanai. It’s also beautifully appointed with vintage tropical wallpaper, a handmade chandelier, and a locally harvested moss carpet.
Camp Magic: Hanalei, Kaua’i
From $4,550 per week; jeanandabbott.com
This perfect-for-families getaway combines the convenience of a prime location – it’s across the street from Hanalei Bay, considered one of the best beaches in Hawaii – with the comfort of light, airy interiors (thanks to vaulted white ceilings and an open great room). The three-bedroom home also offers plenty of alfresco enjoyment, from a hot tub to a spacious lanai facing the ocean.
Splurge-Worthy Sanctuary: Paia, Maui
From $1,499 per night; Airbnb.com
Once ruled by sugar plantations, Paia Town is now a hidden gem of Maui, with hip little storefronts and a gorgeous white-sand beach with world-class windsurfing. You can walk to it all from this beautiful three-bedroom bungalow, however, we suggest penciling in some downtime to bask in the ocean-facing hot tub, dine on the sprawling covered porch and nap in the secluded tree-shaded chaises. Bonus points for those looking for resort conveniences: The house is owned by the Paia Inn, so amenities–from beach coolers and chairs to free gym access–abound.
Tiny Treasure: Kailua-Kona, Hawai’i
From $180 per night; Airbnb.com
The mountaintop setting and swoon-worthy ratio of indoor to outdoor living space (324 square feet to 400-plus, respectively) make this laid-back two-sleeper studio an instant head turner. Sip local coffee at the alfresco dining table and swing in the oceanview hammock at home, or take the five-minute drive down to Kona’s most popular beach–and grab a Longboard Lager at the Big Island’s most famous brewpub, Kona Brewing Company, while you’re at it.
Aolani House: Holualoa, Hawai’i
From $499 per night; Airbnb.com
Enjoy the comfort of a five-star resort villa with the seclusion of a private rental in this beautiful three-bedroom home perched 1,200 feet above acres of coffee farmland. Owned by an interior designer and artist, the home is beautifully decorated without feeling too precious. But, with 180-degree ocean views inside and out, we suspect your eyes might be trained elsewhere. Catch the best sunsets from the sprawling terrace, heated infinity pool, and spa.
Family Fun House: Princeville, Kaua’i
From $399 per night; kidandcoe.com
Outfitted with loads of activities for kids (and adults!) including ping pong and foosball tables, boogie boards, and beach cruisers, this 3,200-square-foot home is paradise for traveling families. The breezy, bright interiors with a pastel palette and reclaimed wood accents are inspired by the beachside setting. The home is also ideally located, just a half block from the famed tide pools of Queen’s Bath and walking distance to the luxe St. Regis—a perfect spot for catching sunsets.
Beachfront Bungalow: Haleiwa, O’ahu
From $300 per night; Airbnb.com
This cozy one-bedroom is blessed with light, bright interiors, coastal décor, and soaring ceilings, but the real gem is out the back door, where the waves crash against the sand a literal stone’s throw from the backyard. The back deck is the perfect place to take in sunsets with a bottle of wine and, in the mornings, Ke Iki Beach is a treasure trove of shells. Leave the car parked and escape on flip-flopped feet: Waimea Bay, Pipeline, food trucks, and beach rentals are all a quick walk away.
Cottage Crush: Poipu, Kaua’i
From $395 per night; vrbo.com
Located in a historic neighborhood just 100 steps from the sandy beaches of Poipu Park, this 1,600-square foot home is inspired by traditional plantation style and laced with modern luxuries (including a high-tech surround sound system). Large doors separating the great room from the spacious lanai fold back, creating a seamless indoor-outdoor living space and welcoming in cool ocean breezes. A fully stocked kitchen, plush king beds, and an outdoor shower add to the resort cottage feel.
Sweet Studio: Kaneohe, O’ahu
From $90 per night; Airbnb.com
This charming studio has all the makings of a cozy vacation home base, and at less than $100, the deal couldn’t be sweeter. Located five minutes from the beach and 20 to Honolulu, the home is convenient while still feeling secluded and quiet. And it includes some attractive perks, like free snorkel gear, beach chairs, and gorgeous mountain and garden views right from the front yard.
Cliff House: Laie, Oahu
From $525 per night; Airbnb.com
While the views from this three-bedroom townhome on the north shore of Oahu are reason enough to hit the “Request to Book” button, the interiors are equally dreamy, with a gourmet kitchen and retractable doors that open out onto the breezy deck. If you still need a push, just read the listing description: “Imagine seeing the crystal-clear waters of Laie Bay from nearly everywhere in the house. Eating breakfast out on the lanai so close to the water you feel like you're standing on the ocean. The gentle waves lulling you into a peaceful sleep while the ocean breezes envelop you. This is the Sea Cliff House.”