Published September 18, 2020 9/18/2020

15 Dreamy Vacation Rentals in Hawaii

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

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.

YOU'RE ALL SET!

Look out for our newsletters in your inbox soon.

Bamboo Temple, Maui Bamboo Temple Airbnb, Maui
Credit: airbnb.com
Bamboo Temple Airbnb, Maui

Bamboo Temple, Maui

If you’re looking for something unique and adventurous that allows you to immerse yourself in nature, the Bamboo Temple offers an eco-retreat on what’s called the “Greenest Spot on Maui.” More of a glamping experience, the one-bedroom, one-bath accommodation is one of the top Airbnbs in Maui. It is shaped like a nautilus and sits right next to the Pacific. Large windows showcase the Hana coast and the sea, while stone staircases lead to a deck. It has a four-poster bed, a kitchen and an outdoor shower, while the surrounding grounds include hiking trails and waterfall lagoons for romantic dips. Yoga and meditation classes are available too.

The Gingerbread House, Maui Gingerbread House Airbnb, Maui
Credit: airbnb.com
Gingerbread House Airbnb, Maui

The 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, 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: VRBO.com
5 Star Oceanfront Maui, Hawaii

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 is 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.

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

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, cooler for storing food/drinks, and a coffee maker.

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

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.

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

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.

Turtle Hut I at Punalu'u Black Sand Beach, Pahala Turtle Hut I at Punalu'u Black Sand Beach, Hawaii
Credit: VRBO.com
Turtle Hut I at Punalu'u Black Sand Beach, Hawaii

Turtle Hut I at Punalu'u Black Sand Beach, Pahala

The Turtle Hut was named for the endangered hawksbill turtles that come to rest on the property’s black sand beach. Enjoy relaxing with them among the gorgeous views while perched on a bluff with Mauna Loa Volcano in the background and the Pacific in the front. It’s a secluded oasis between Kailua-Kona and Hilo, just 30 minutes from Volcano National park and includes one-bedroom plus a sofa bed, sleeping up to four guests who also enjoy 15 percent discounts off KapohoKine Adventure Tours.

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

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 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: airbnb.com
Hale La-Air Conditioned Luxury Ocean Home

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.

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

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 relaxing 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.

Oceanfront Ground Floor Corner Vacation Rental, Kauai Oceanfront, Ground Floor Corner Vacation Rental, Kauai
Credit: VRBO.com
Oceanfront, Ground Floor Corner Vacation Rental, Kauai

Oceanfront Ground Floor Corner Vacation Rental, Kauai

Located in Poipu Beach, this one-bedroom oceanfront condo is a corner unit providing stunning ocean views from walls of windows. Every room has its own ocean view, and from the patio all you’ll need to do is walk 20 feet across the lawn to the seawall and you’ll be at one of Hawaii’s top surf breaks. Just to the left is Turtle Bay where you’ll see turtles swimming in the shallow water. You’ll be able to wake up to a view and enjoy many amenities, including a washer/dryer, air conditioning and cable TV.

Sea Cliff House, Oahu Sea Cliff House Maui Airbnb
Credit: airbnb.com
Sea Cliff House Maui Airbnb

Sea Cliff House, Oahu

The Sea Cliff House offers the incredible experience of sleeping as if you were right on the ocean. It seems to extend over the waters of Laie on the island of Oahu, allowing the waves to lull you to sleep while enjoying cool ocean breezes too. The lanai is right over the water where sea turtles swim below. It sleeps up to 10 in three bedrooms with seven beds and includes a gourmet kitchen, cable TV, Wi-Fi, and a washer/dryer.

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

Beachfront Solar Home, Oahu

Ideal for surfers, the Beachfront Solar Home sits right in from 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.

Cabana on the Water, Oahu Cabana on the Water, Oahu
Credit: Airbnb.com
Cabana on the Water, Oahu

Cabana on the Water, Oahu

This one-bedroom cabana accommodates up to four and is just steps from the water’s edge. Guests enjoy access to a shared dock, pool and yard, including a tropical garden for picking and eating the fruit in season. It offers indoor and outdoor dining on the lanai right next to the water, along with Internet TV, a washer/dryer,  and kitchenette with a full-sized refrigerator, dishwasher, microwave, a variety of small kitchen appliances, and everything you need to make your own meals.

North Shore Surf House, Oahu North Shore Surf House, Oahu
Credit: Airbnb.com
North Shore Surf House, Oahu

North Shore Surf House, Oahu

You’ll be able to wake up and gaze out at the waves from this oceanfront beach house on the North Shore. It offers sweeping views from the famous Pipeline all the way to Sunset Beach’s West Peak. There are views galore, from the ocean view master bedroom with a personal surfboard rack, to the wall to wall windows and sliding doors in the living and dining rooms. In the fully equipped kitchen, you’ll not only have all the essentials but a Nespresso machine and milk frother. Enjoy private beach access to the area’s most consistent surf spot and a child-friendly swimming area too.

You May Also Like
The Best Cabin Airbnb in Every State By K.C. DERMODY | SEP 30, 2020

Powered by: Strive Media

YOU'RE ALL SET!

Look out for our newsletters in your inbox soon.

Oops!

Please fill out highlighted fields and click "Compare Prices" to continue.