West of…Hawaii

I love vacation planning. Even when they’re not my vacations. I like pretending they’re mine. I mean this in the most uncreepy way possible, of course. I will often hear about a friend’s upcoming trip somewhere and think, “What would I do if I was going there?” And then I dedicate an evening daydreaming about travel. …And I am really, really sad for myself now that I’ve heard that out loud.

Today’s pretend vacation is to the magical shores of Hawaii – Maui or Oahu, to be specific. My lovely boss is getting married soon and they’re planning their honeymoon. So I decided to window shop. Monica, I promise not be lurking behind the curtains at any of these places should you choose to pursue them. I will be dutifully holding down the fort at my desk, totally NOT surfing the internet looking at pictures of white, sandy shores and turquoise waters.

We visited Oahu together about five years ago and it was our favorite trip ever. We stayed in a hotel that time and it was lovely, but since then, we’ve developed a love for the personal feeling of living like locals in AirBnB spaces around the world. (This link will give you $25 off your first booking, too! You’re welcome.) Finding good-looking apartments or homes near beaches is infamously difficult. Partially it’s due to the constant humidity and the fact that doors and windows are open to the elements so often. People don’t always buy pretty things and the weather-hardy things are not very pretty. And partially it’s because there’s the assumption that you’re only there to look at the view. Yes and no. I like both an inspiring view and a space that captures a new part of my imagination. Here’s my top 10 favorites:


1. Secluded Beach Bungalow // $169

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2. Octagon Studio // $235

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3. Kailua Beach Studio // $200

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4. Dwell-Style Mountain Retreat // $160

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5. Kailua Beachside Cottage Here and Here // $200

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6. Ginger Falls // $185

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7. Modern Condo // $160

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8. Hunakai Cottage // $213

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9. Leeward Ocean-Front Condo // $135

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10. Hawaii Surf-Inspired Home // $170

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You can see these and a few more picks for Oahu and Maui here. If you’ll excuse me, I’m going to go back to mentally sunning myself on Lanikai beach now.

If you’re going on a trip and you want me to do a post scouting out some fun places to stay while there, shoot me a message or leave me a comment!


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