My boyfriend and I want to rent a small cottage or something for two people in Hawaii. We don’t know which island. We want to just enjoy the quite beaches and maybe go out at nights. Can someone help me find the right island/city and websites to rent a place to stay for 3 to 5 days. Thank you


I’ve used to site below to find a cabin elsewhere in the country, but they sure have a lot of listings for Hawaii. One very convenient feature they have added recently is the ability to narrow down the listings to those that are available between the dates you specify. This shows up when you look at specific neighborhoods on different islands.
To give you an idea of the quiet/nightlife balance, I’ve arranged neighborhoods in a kind of spectrum for you. In that list, Hawaii refers to the island of Hawaii, also called the Big Island.
But on Molokai, for example, you could go to the Kualapuu Cookhouse on Thursday night and watch people come play ukulele, washtub bass, slack-key guitar, and sing, still wearing grease-stained t-shirts from work. Or you could go to the Hotel Molokai on Friday night to see about 12-20 “kupuna” gather to make music. Unfortunately, the Lodge in Maunaloa closed back in 2008, and Paddler’s Inn just closed, and but we are hopeful it will reopen soon.
Quiet
Lanai; Molokai; Rural Hawaii
More quiet than nightlife
Kauai; Hilo, Hilo
Quiet, some nightlife
Lahaina, Maui; Kailua-Kona, Hawaii; Windward Side Oahu
Nightlife
Kihei, Maui; Honolulu and Waikiki, Oahu

2 Responses

  1. I don’t think there are a lot of small cottages around. There are vacation houses, usually 3 bedroom, and there are bed & breakfasts. I would recommend a bed & breakfast in Kailua or Lanikai on Oahu. The beaches are great & you are within about a half hour’s drive of Waikiki, so you can get to the nightlife.

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