Our research is editorially independent but we may earn a commission for purchases made through our links.

15 Dreamy Vacation Rentals in Hawaii

One of the most important decisions anyone can make when planning a vacation in Hawaii is where to stay. Should you book a room at a luxury resort or hotel or a vacation rental property? While they all have their own benefits, a vacation rental can be ideal as it usually provides a kitchen for cooking your own meals, more space and more privacy. These dreamy vacation rentals are sure to fit the bill whether you plan to stay in Maui, Kauai, the Big Island or Oahu.

Garden Gingerbread House, Maui Gingerbread House Airbnb, Maui
Credit: Gingerbread House Airbnb, Maui by airbnb.com

Garden Gingerbread House, Maui

A top-rated Airbnb in the U.S. with a secluded setting, the Gingerbread House is a renovated 1930s studio cottage that lies along the northwest slopes of Haleakala in a lush gated property. You’ll have access to 4.5 acres that include an organic veggie start farm with many fruit trees, including mango, papaya, passion fruit, banana, coconuts and guava, while the beach is just 10 minutes away. The home has a cedar interior, a small kitchenette and a custom-tiled bathroom, along with an outdoor patio that sits underneath a tree canopy for shade. It sits adjacent to The Sacred Garden with walking labyrinths, lily ponds and meditation zones.

5-Star Oceanfront, Maui 5 Star Oceanfront Maui, Hawaii
Credit: 5 Star Oceanfront Maui, Hawaii by VRBO.com

5-Star Oceanfront, Maui

This one-bedroom condo is truly right on the ocean, with the waves crashing just below the lanai. It includes a one-bedroom with a queen-size bed and a queen-sized sofa bed in the living room, sleeping up to four guests. Look forward to waking up to glorious sunrises over Mount Haleakala and, throughout the day, spectacular unobstructed views of Maalaea Bay, Molokini crater crescent, Kihei, and Mount Haleakala. The unit is fully air-conditioned and includes cable TV as well as access to swimming with a view of the Pacific in the large heated pool.

Oceanfront Haena Cottage Steps to the Beach - Hanalei, Kauai Oceanfront Haena Cottage
Credit: Oceanfront Haena Cottage by Airbnb.com

Oceanfront Haena Cottage Steps to the Beach - Hanalei, Kauai

Located in one of the most spectacular areas of Kauai, this secluded paradise is just five steps from the beach, lying adjacent to Tunnels Beach, often named among the most beautiful on the island. You’ll enjoy panoramic ocean views from every room in a prime spot for watching humpback whales in the winter. Sea turtles make an occasional appearance, too. Look forward to spending some time in the oceanfront bathroom where you can soak while gazing out at the Pacific. Other highlights include a comfy couch to relax on while taking advantage of the 50″ flat-screen TV with Hulu and Netflix while ocean views feature in the backdrop. There’s a full kitchen with stainless steel appliances and a washer/dryer too.

Eco-Chic Tropical TreeTops Villa - Kalaheo, Kauai Eco-Chic Treetops Tropical Villa
Credit: Eco-Chic Treetops Tropical Villa by Airbnb.com

Eco-Chic Tropical TreeTops Villa - Kalaheo, Kauai

This Polynesian villa is nestled in the hills on an 11.5-acre property, providing a honeymoon-worthy oasis complete with spectacular ocean and mountain views. It’s surrounded by abundant flora and fauna, including rare native plants, birds, and butterflies, yet it’s just 20 minutes north of Poipu, often named among the most beautiful beaches in the U.S. The interior is impressive thanks to the owner’s collection of art, artifacts, and unique furnishings acquired on voyages across the globe. The bedroom is a highlight with a four-poster CalKing bed where you can wake up to a view of the endless green hills rolling into the blue shades of the Pacific. There’s also a full kitchen with all you need to make your own meals, a washer/dryer, fabulous outdoor living spaces, and access to a shared pool.

Dreamy Tropical Tree House, Fern Forest Dreamy Tropical Tree House
Credit: Dreamy Tropical Tree House by airbnb.com

Dreamy Tropical Tree House, Fern Forest

Located just 10 miles from Volcano National Park, this secluded, off-grid bamboo treehouse is nestled among a canopy of local flora. A perfect Airbnb for honeymooners, it features a hanging bed on the ground level, suspended underneath, where you’ll find a staircase that leads to the “trapdoor.” Enter to find yourself on the lanai among the canopy of trees, enjoying a 360-degree view of the jungle. Inside the sliding glass doors is the bedroom with large windows and doors flooding it with natural light. Absolutely magical, you’ll have a natural rainwater shower, while electricity is generated by sunlight. It also includes a kitchenette with a sink, a cooler for storing food/drinks, and a coffee maker.

Kehana Point Cliff House, Pāhoa Kehana Point Cliff House, Pāhoa
Credit: Kehana Point Cliff House, Pāhoa by airbnb.com

Kehana Point Cliff House, Pāhoa

This unique two-bedroom home, accommodating up to six guests, has been featured on the Travel Channel and HGTV’s “Off Beat American.” It definitely stands out, set atop a lava cliff at Kehena Point, jutting out into the Pacific further than the cliffs that surround it, providing unbeatable views of the coast in both directions. You’ll be able to watch for whales between November and April and walk to a black sand beach. The upper lanai is ideal for star-gazing, whale watching, and sunbathing. All rooms have windows that offer sweeping ocean views. You’ll also have all the comforts of home, including a full kitchen, TV and Wi-Fi.

Beautiful Oceanfront View, West Maui - Maui Beautiful Oceanfront View West Maui
Credit: Beautiful Oceanfront View West Maui by Airbnb.com

Beautiful Oceanfront View, West Maui - Maui

This oceanfront studio is a hidden gem nestled between Ka’anapali and Kapalu, away from the big resorts, offering a quiet setting and a breathtaking ocean view. It’s one of the best values you’ll find on Maui, complete with a huge lanai where you’ll have a front-row seat for watching the whales during the season, from December through March. Just a minute on foot will bring you to a small secret beach in one direction, while a five-minute walk in the other leads to a stretch that’s a local’s favorite. The studio accommodates up to two and comes with all the essentials, including a full kitchen, fast Wi-Fi, a Smart TV, and a washer/dryer. Plus, there are many complimentary extras, from hiking poles and a daypack to snorkeling masks and fins, beach chairs, and an umbrella.

Romantic Treehouse in the Hawaiian Rainforest - Volcano, Big Island Walk into a whole new world here
Credit: Walk into a whole new world here by Airbnb.com

Romantic Treehouse in the Hawaiian Rainforest - Volcano, Big Island

Perfect for romance-seeking couples, this dreamy treehouse is tucked into the rainforest just outside Volcanoes National Park. It sits in a park-like setting and offers enticing outdoor living spaces, including a covered outdoor lounge and a lanai on the top floor where you can gaze out at the unique local flora. There’s an indoor/outdoor shower too. Inside, you’ll love the hardwood floors and floor-to-ceiling windows, while the hanging rattan chair is perfect for relaxing and enjoying a little quiet contemplation. There’s no TV, but you’ll have Wi-Fi and a full kitchen.

Direct Oceanfront Custom Home, Captain Cook Direct Oceanfront Custom Home
Credit: Direct Oceanfront Custom Home by VRBO.com

Direct Oceanfront Custom Home, Captain Cook

This two-bedroom oceanfront custom home sits at sea level in the last fishing village of quiet, rural Milolii on an ancient lava flow 33 miles south of Kailua-Kona. It accommodates four and is so close to the water that powerful waves spray all the way above the deck. You’ll hear the whales before spotting them (in season), along with green sea turtles, spinner dolphins and the occasional manta ray, year-round. The home includes kayaks and snorkel gear, a George Foreman Electric Grill and a beautiful Polynesian design.

Tropical Beach Getaway, Kauai Tropical Beach Getaway, Kauai
Credit: Tropical Beach Getaway, Kauai by Airbnb.com

Tropical Beach Getaway, Kauai

This one-bedroom home sits on Kauai’s south shore in one of the most popular spots, Poipu Beach, ideal for snorkeling, diving and spotting monk seals. It offers beautiful sunrises, sunsets, an island breeze and a backdrop of mountain views along with lush tropical surroundings. Perfect for a romantic couple’s retreat, it includes a king-size bed and a living room area divided by French doors for additional secluded privacy. There’s even an outdoor pro putting green and putting holes that light up at night, along with a waterfall pond and hammock.

Hale La-Air Conditioned Luxury Ocean Home, Kauai Hale La-Air Conditioned Luxury Ocean Home
Credit: Hale La-Air Conditioned Luxury Ocean Home by airbnb.com

Hale La-Air Conditioned Luxury Ocean Home, Kauai

This luxury vacation home is ideal for a large family, family reunion, or a group of friends, with five bedrooms accommodating as many as 11 guests. You’ll be just steps from white sand beaches, boat tours to the Na Pali coast and hiking in Waimea Canyon. It includes snorkel gear, a beach umbrella, beach towels, and beach chairs, along with cable TV, a washer/dryer, a large kitchen with everything you need to cook your meals and much more.

Sunset Beach House - Haleiwa, Oahu Sunset Beach House
Credit: Sunset Beach House by airbnb.com

Sunset Beach House - Haleiwa, Oahu

You’ll be surrounded by magnificent ocean views when staying in the Sunset Beach House. It offers breathtaking sunset views and direct access to the sand and the surf, while some great food trucks, a bakery, and a grocery store are only a short walk away. You’ll have an outdoor shower and a grill for cookouts, a full kitchen, 55″ HDTV with cable channels, and a washer/dryer too.

Luxurious Waterfront Airbnb, Kauai Luxurious Waterfront Airbnb, Kauai
Credit: Luxurious Waterfront Airbnb, Kauai by Airbnb.com

Luxurious Waterfront Airbnb, Kauai

This stunning secluded hideaway for two sits on a private knoll, providing incredible panoramic views of lush mountains and the sea. Aptly referred to as Hale Lani, “Heavenly Home,” it’s set across 34 private oceanfront acres on Kauai’s most exclusive road where A-list celebrities own homes or stay on vacation. Enjoy the tropical gardens and relax on the northwest-facing lanai with panoramic views of sunsets and the Pacific. It includes a gourmet kitchen with high-end appliances, one bedroom with a Cal-King bed and floor-to-ceiling sliding glass doors showcasing more awe-inspiring ocean view.

Waipio Ocean View Oasis - Waipio, Big Island Hot Tub at Waipio Oasis
Credit: Hot Tub at Waipio Oasis by Airbnb.com

Waipio Ocean View Oasis - Waipio, Big Island

Far from any high-rise resorts, this rental is truly an enchanting oasis, offering a tranquil setting that’s just a short drive from historic Honokaʻa and within walking distance of one of the most scenic places on the Big Island, Waipio Valley. It sits on a private, fenced one-third of an acre property and comes complete with an ocean-view hot tub. In the winter, you might even spot whales while soaking, and after dark all year round, the stargazing is incredible. There’s a large, furnished ocean-view deck that can be accessed via French doors from the living room and bedroom, while the inside has a cozy, homey feel with Zen decor and all the modern comforts.

Pipeline Beachfront Solar Home, Oahu Beachfront Solar Home, Oahu, Hawaii
Credit: Beachfront Solar Home, Oahu, Hawaii by Airbnb.com

Pipeline Beachfront Solar Home, Oahu

Ideal for surfers, the Beachfront Solar Home sits right in front of the world-famous Pipeline, Backdoor and Off-The-Wall. Those who just want to swim will appreciate it too as most of the time the waves are calm and the beach quiet. The two-bedroom home sleeps up to seven with the addition of a Murphy bed in the living room and is 100 percent solar-powered. It has an open floor plan with a fully equipped kitchen as well as a large deck, grill, washing machine, a cable TV with a DVD player, stereo and all sorts of beach toys, including snorkel gear and boogie boards. The host also rents a variety of surfboards, both long and short.