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Only one block from the beach, this riverside canal cottage on the outskirts of Kapaa Town overlooks the peaceful banks of the Wailua River, where guests can paddle with host-provided kayaks and SUPs, or take bikes out for a spin on a lovely path. The river leads to a natural lava rock grotto with waterfalls, an area formerly reserved for Hawaiian royalty but now enjoyed by many.
The plantation-style cottage was built in 1953 but renovated to feature beautiful paneling and beam details, bamboo accents, air conditioning, a vaulted ceiling with fan, sustainable wood floors, and a well-appointed outdoor area with a grill and water views. The lush grounds are home to fruit-bearing trees, so don't be surprised if the host offers you a taste of starfruit.
The kitchen is stocked with all the basics, so you'll be able to sample local coffee and have seasoning on hand to flavor your in-room meals. Beach chairs and umbrellas are also provided, and there's complimentary guest laundry.
Private guest house on Maui
AirbnbTypical starting price: $172
Town: Kihei
Sleeps: 2 guests/ 1 bedroom
Rating: 4.93
Some of Maui's most beloved beaches are located in Kihei and Wailea-Makena, and this one-bedroom cottage makes it easy to take advantage of the waterfront along Keawakapu and Kamaole Beaches where you'll find food trucks and casual eateries aplenty, along with great people watching.
The space is bright, light, and sparkling clean with a convection oven and enough kitchen space to cook meals. There is also a coffee maker, air conditioning, a memory foam Queen-sized bed, and blackout curtains for excellent sleep. The private courtyard space includes a BBQ and hammock surrounded by lush plant life including organic papayas, mangoes, avocados, lilikoi, guava, lemon, and lime, depending on the season.
Additionally, the living room has a mounted smart TV to stream your favorite shows and movies after a long day at the beach. This guest house is attached to the host's home, but you will have incredible privacy with a separate entrance and your own dedicated outdoor space.
Modern remodeled condo at Poipu Beach, Kauai
AirbnbTypical starting price: $179
Town: Koloa
Sleeps: 4 guests/1 bedroom
Rating: 4.92
It doesn't get much closer to the waterfront at Poipu Beach than this stunning home.
Fresh off a full remodel, the contemporary space has a cool palette of white and grey, with a stainless fridge and in-counter cooktop, ideal for quick self-made meals. Adorning the walls is a series of island images from a locally renowned photographer, and the fresh, clean design carries throughout the condo.
There is a large bath offering natural light and the main bedroom has a King-size bed and a spacious layout. The living room convertible sofa adds extra sleeping space, and big windows and air conditioning keep the space comfy and cool.
In addition to immediate beach access, the condo property also has an outdoor grill and seating area for meals outside, while guests are also close to popular ice cream shops, casual and upscale restaurants, and great local coffee roasters.
Bohemian retreat on the Big Island
AirbnbTypical starting price: $182
Town: Captain Cook
Sleeps: 4 guests/2 bedrooms
Rating: 4.89
Set on an organic mango orchard and surrounded by plumerias, the home is located in Captain Cook and just a mile from Kealakekua Bay, known for some of Hawaii's best snorkeling and wild dolphins.
Kind of like glamping, this open-air, two-bedr
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