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A Five-Step Guide to Booking Your Dream Stay

A Five-Step Guide to Booking Your Dream Stay

Jun 06, 2019

With summer almost here, many of us are in last-minute vacation planning mode. While hotels offer a range of amenities, there’s nothing quite like what a home rental offers—personal space, dedicated areas to cook and even entertain, and the ability to live like a local immersed in the fabric of the culture. However, not all homes are created equal. Today we sat down with design journalist and lifestyle expert Jen Woo to discuss some some tried-and-true tips on finding the best vacation rental.


Airbnb, Homeaway, VRBO, Expedia…there are so many booking platforms offering vacation rentals, how do you pick a platform?

I’m a creature of habit, and for the most part, I find myself booking on Airbnb. The filters on Airbnb are more comprehensive than the other sites. Not only can I sort by amenities like a pool, WiFi, or a laptop friendly workplace, but they also have fun filters like “unique homes” or dog-friendly options since I often travel with my pup. Airbnb has also recently introduced a program called “Airbnb Plus” which requires hosts to meet a quality checklist that includes things that you might expect out of a boutique hotel like a keen eye for design (for the gram) and top rated reviews. Most importantly, Airbnb inspects these homes individually so you know you’ll be in good hands.


There’s no better feeling than feeling like you got something for a steal. I come from a background of bargaining fiercely in bazaars be it in Hong Kong or a Moroccan souk, and I’m a sucker for a good deal. I have noticed that a lot of homes will be listed on both Airbnb and other sites like VRBO or Homeaway, and recommend price comparing as the same stay may be listed at different nightly rates on different sites.


Finally, if you are someone who really loves rewards points, platforms like Expedia, for example, allow you to use your Expedia rewards points towards booking costs or earn rewards when booking. Expedia also has quite a few homes for rent, so it’s worth checking out.


So filters are important. What are some of your most commonly applied filters?

Three things: dog friendly, reliable check in, and design with a nook where I can see myself planted for a while as I’m always on my laptop.


My husband and I frequently travel with our fur baby, Yogi. He came with the house we rented while living in Costa Rica Costa Rica. We had a little beachside loft in Santa Teresa where there were dirt roads and the electricity was in and out; however, we always had warm water to swim in, good waves, tons of yoga, and delicious food. He’s a musician, and we’re always working on our individual projects while on the go. Yogi has flown with me to stay in the north of Spain, and has traveled up and down the West Coast with us.


Reliable check in is an element of Airbnb Plus that I really love. I’m constantly balancing all the details of our trips, and check in is one of those friction points where hotels have traditionally won. It can be really challenging to have to meet up with a host or a host’s friend to let you in, especially if you’re traveling at weird hours. When a host’s property is equipped with a smart lock, the whole trip just gets off to an easier start. Coming and going is also much easier. It’s so nice to have to remember to bring a key while leaving for the day, or coordinate sharing a key if we’re staying with people.


Due to the nature of my profession as a freelance writer, content creator, and brand consultant, the work never ends! Airbnb’s “laptop friendly workplace” is a lifesaver. I’m always on the hunt for a good desk, cozy corner to work in, or a workspace with a view. One of my favorite places was just a quick drive north in Sebastopol. We were spending a weekend there and found a quaint little cottage on a redwood property alongside the owners’ main house. The area was fenced with several acres of redwoods so our dog was able to roam freely and play with their pup, Alfie. There was also the most perfect work nook situated against a floor-to-ceiling octagonal window that looked out onto the wooded grounds. It was the perfect place to sit and write, and then I could also easily pop out for a dip in the pool, a game of bocce, or a hike!


What about amenities? There seem to be a million you can tick off—which are the most important to you?

Design is a big one for me. I tend to lean more towards minimalist places so the space feels airy and clean—to combat the business of my mind from work so I can actually decompress. While not a necessity, I love having my own bedside table and light so I can sit in bed and read or work if my husband decides to get to sleep before me. Closet space or a clothing rack is also nice so I don’t end up with a wild pile of clothes in my suitcase.


I also really enjoy staying in homes where the host has gone the extra mile. For example, in Joshua Tree, the host created a handmade booklet with illustrations of the town including a map, plant guides, and places to visit. In New Orleans, we were greeted with wine and waffle mix, which we definitely took advantage of after late nights out. Luxe details are always nice too—like a hot tub, rainfall shower, and nice linens. Other no brainers are nice toiletries or neighborhood guides—basically the elements you’d expect from a boutique hotel.


How important are reviews? Do you read pages of reviews, or just a few?

Reviews are key. I’m a huge proponent of reading about other people’s experience and do this for everything whether it’s buying a pair of shoes or finding a place to stay. However, it’s easy to fall into a review trap and end up reading pages upon page. Some sites will smart filter them for you though, and bubble up the most helpful ones by votes. I tend to be a bit more skeptical, and sort by date, reading the most recent first, and then if there’s a glaringly negative review, I typically dive a little deeper and see if any of the other negative reviews mention the same pain points. If more than one negative or neutral review complains about the cleanliness, I typically skip it. Reviews are another factor where multiple platform listings come in handy. When a property is listed on both Airbnb and VRBO for example, I cross reference reviews to see if the sentiment generally matches up.


Thanks for all these tips. Anything else you’d like to add?

Location is another factor that plays a major role. I like to find places that are actually in the areas where I’d like to spend time, but also offer respite after a day or night of being out. That means being immersed in the fabric of the destination, like a hip neighborhood and close enough to the action, while also being able to really take a break from it in a quiet space. Take a look at the map when selecting a location and its proximity to things you’d like to do as well as to public transit so you can easily explore.


Jen Woo is a regional correspondent for Architectural Digest, contributor at Dwell, Lonny, and 7x7, and a brand consultant and content creator. She also runs her own independent publication, Rogue Habits, documenting the curious and creative.