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Living in an Airbnb for a month

Hillcrest at night.

Growing up I always heard how amazing and beautiful San Diego was from my dad. After Vietnam, he was stationed there for 2 years and fell in love. After he passed away in June 2017, I took my first trip to San Diego and fell in love. Fast forward two years later and a few more trips to San Diego and I love it even more now than I did then.

In February 2019, while in San Diego for a user conference I was producing, I met up with my dear friend and while sipping hot cocoa in a cute cafe during a rainstorm, I started thinking “gosh, I could live here”. Back and forth I went through the pros and cons: pros: sunshine, mountains, ocean, warmth, dads fav city, new experiences and friends to make, great job market, that coastline cons: far from my family and my best friends plus there is a part of me not ready to give up on NYC and the one who has my heart. I always had many pros but, the cons I had were hard to swallow.

After a wonderful week, I flew back home but, the thought of spending more time in San Diego was constantly on my mind. So, after going through the pros and cons one last time, I took a risk and on March 30, 2019 I decided I was going to live in San Diego for 21 days in an Airbnb. This is the best way to really see what it would be like to live and work there and if my love is a temporary/only when traveling feeling or deep and permanent.

To figure out where I was going to stay, I pulled out my laptop and started browsing:

  • Safest neighborhoods in San Diego
  • Walkable neighborhoods in San Diego
  • New Yorker in San Diego

The amount of search results I pulled up was insane. Seems I am not the only one looking this up! One site I came upon that stuck out to me was It not only had walkable and safe locations but, information about each. Summary of the area, places to eat/drink, cultural attractions, types of housing, etc.

I narrowed my search down to two areas: Hillcrest and East Village. Mostly because they look eclectic, full of culture and people my age. However, a part of me chose those because they remind me the most of my home, NYC.

I was not going to just let a website decide where I was going to live for a month so, I asked local friends their opinions. After learning that my friend’s daughter lived in Hillcrest and loved it, I decided that it was the place for me. And let me tell you, it did not disappoint.

Hillcrest at night. Photo by rabbot
Hillcrest at night. Photo by rabbot

Hillcrest is known for its restaurants, bars, shops, and vibrant LGBTQ community. Already, I felt like I was at home! It is right near Balboa park, which is filled with the famous San Diego Zoo, Gardens, walking trails and much more. Also, a great gym is right up the road from where I stayed. It was perfect!

Alright so, the neighborhood was selected but, now where the heck was, I going to live. My criteria to make it less of a vacation and more like I am living in San Diego was:

  • Must have a solid internet connection. I work remotely so, it’s a blessing I can even do this. I MUST make sure nothing slows me down from doing my job.
  • A functional kitchen. I do not want to eat out for every meal.
  • My own space. I did not want to rent a room in someone’s house. Rather a studio, guest house or whole apartment.
  • Living space for nights I want to lounge out.
  • Well-lit street. As much as you can do research, you do not know the area until you’re there.
  • Unique Southern California vibes. I wanted a bungalow.

I was in luck when I started putting my filters into Airbnb because there were quite a few solid choices.

  • A 2-room vacation home – full kitchen – internet and parking. However, the home was attached to a house with 3 kids. Nope, not doing that.
  • A full apartment right on 5th ave. All I could need in a long-term home for $2800. No, thank you! I do not even pay that much in NYC.
  • A studio bungalow, on a hill, with a kitchen, internet and Zen garden for $2000! YES!!!!

Now $2000 sounds like a lot, even for me. However, this is $500 less that my monthly NYC expenses when you factor in WiFi, cable, utilities and parking being included. I will not have a car but, I at least know I have that option. Check this baby out!

Living in San Diego was an amazing experience. Event short term. I hope my story inspires you to do the same. No one ever knows how life is going to go or when it is going to end. So, live it. Enjoy it. Explore it.

Happy exploring


Sara Straw @solotravelwoman



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