Airbnb Booking Guide: 9 Essential Tips Before You Book Your Rental
Perfect for Solo Retreats and Weekend Getaways
I’m a boutique inn, small hotel kind of girl. But, sometimes a vacation rental makes the most sense. Perhaps it’s a big family gathering, or you are in a town where the only hotel option is a big-box hotel, etc.
Whether you're seeking a cozy cabin retreat or a chic city apartment, choosing the right vacation rental can make or break your trip. After years of both amazing discoveries and hard-learned lessons, I've developed a system for choosing Airbnb/VRBO properties. Here's my step-by-step guide. (note - I am very picky particular on this topic)
When looking for a rental rather than a small, adorable inn, I am usually doing a solo retreat. But whether it is for fun or work,I think you must answer these two questions before you begin planning:
What is the purpose of the trip/visit?
What are your non-negotiables?
Get those two things figured out first, and you have already eliminated half the rentals out there - and this is good, because you wouldn’t have been happy in those, anyway.
If you’re doing a retreat/offisite around work, you most likely are hoping for a quiet place that also has inspirational vibes, few distractions, a place where you can think, where you can spread out with papers, books, a computer and monitor, etc.
Thus, for this sort of trip, my non-negotiables are:
A good workspace.
A covered outdoor space.
Some sort of view (can be a beautiful yard)
And then, I go through each step:
1 | Reveal the full price upfront and set filters
Before falling in love with a listing, click "Show total price" to see the complete cost, including cleaning fees and service charges (usually tax is not included). That $200/night steal might actually be $897 after all fees are included.
You can also set filters. Sometimes I leave this alone unless I am getting so many listings that it would help to narrow it down. Since you’ve answered your reason and your non-negotiable questions, you could filter that you only want a house with a a water view, or with a porch, free cancellation, etc.
One thing I do like to set up in the beginning is the type of property. I usually don’t care if it is a cabin vs. a townhouse, etc., but I don’t want a room in someone’s house where they are also there. So, I click the filter that usually says something like “the entire place to yourself.”
2 | Use the interactive map
Once you answer your two questions above (your purpose and non-negotiables), you will know where you want to be. Are you sightseeing and need to be close to everything, or are you trying to escape? Do you need water views? Walking distance to restaurants, etc? I find it easiest to check the box that says “move with map” and go from there.
If you follow these steps, you will most likely avoid scam listings, but a legitimate listing should have a functioning, interactive map that moves and zooms smoothly. If the map seems glitchy or won't respond to your clicks, this could be a red flag indicating a problematic or potentially fraudulent listing.
3 | Quick photo scan and the facts
Start with a quick glance at the photos, and then read about the space to get an initial feel. the host will probably tell you basic information about the house, if it is shared, etc.
I like a host who gives a description that is filled with detail and personality - it is a great preview to your experience.
I address this in the next step, but I am typically only looking at properties with a rating of 4.9-5.0, nothing lower. Maybe, maybe I’ll look at a 4.87, but rarely.
4 | Review the reviews
As I just said, I only look at properties with a 4.9 or higher – anything below suggests potential issues. (I know - it’s high and doesn’t always guarantee success, but I’ve learned the hard way)
One exception to the 4.9+ rule: if the rental is new with only a handful of reviews, with one person giving it a one-star rating and everyone else giving it five stars, then chances are that the one-star reviewer complains about everything.
You can also filter what you see by choosing to see only “Guest Favorites” or sometimes called “Top Hosts".” You can learn a lot from the reviews and other guests - shops and restaurants that are within walking distance, where you can see the sunrise, if the host generally leaves snacks, etc. This will typically show you only highly-rated properties.
You might see that multiple guests thought the bed was uncomfortable or that the nearby train kept them up at night. Maybe it is “the entire house” but the hosts live above and you can hear them and their dog. None of this is necessarily bad, but it’s good info.
And, just like a hotel, the hosts should be responding to these reviews. A bad review really hurts them in the Airbnb world, so be sure to read their responses. Yes, some people are just negative nellies and have to complain about something, but once you read several, you will know when there is an issue - trust that!
Sorting the reviews from lowest to highest can clarify what others had issues with, and then you can decide if they matter to you.
TIP: Recently, I have been finding more and more rentals where there are almost “apartments” within a house and you might share the front porch. Or, there are two cabins on the same property, and the guests share an outdoor space, etc. This isn’t always bad, but if you don’t want this, pay attention, as the host should tell you in the info.
Some of my rentals for solo retreats - I love that covered outdoor space!
5 | Back to the photos and info
And then the fun part - a deep dive into the photos - this will tell you a lot if you look at them carefully. Look beyond the staged beauty shots and examine practical details: bathroom cleanliness, kitchen appliances, bed quality, storage space, and natural lighting.
Pay attention to photo angles – sometimes they're used to hide small spaces or unflattering views - similar to real estate photos.
Check if photos match the written description and seem current rather than outdated. If the quality is bad, then it says something about the host.
The aesthetic, the vibe, and even the quality of the furniture is high on my list of values in a rental, so I look closely at this.
This reminds me of something else: I do want a sense of place. Anything that feels corporate/Hilton/traditional management company is usually not what I am looking for. If I’m doing a solo offsite, I am most likely in the house all day. Thus, I need a view. I need covered outdoor space, etc.
If I were on vacation at the beach, I might be looking at views, outdoor shower, includes a golf cart, etc.
So, check this against your non-negotiables.
Yes, that is a baby grand piano in the rental!
6 | Check out the host
Look at how many years he/she has been hosting. Scroll all the way to the bottom and see their picture and a bit of info. You can click on their photo at the bottom and it takes you to more info, as well as any other listings they have. This can prove helpful, especially if the property you are considering is new and doesn’t have many reviews.
You can also message the host without booking. Maybe you have an elderly parent with you and need to make sure the shower is walk-in with a grab bar, etc.
7 | Look at the Policies
I check the cancellation policy because, well - life happens. If I am booking weeks out or if I know several things in life are up in the air, I will choose a place with a more lenient policy. For important trips or uncertain times, consider flexible cancellation even if it costs slightly more.
Sometimes, I might check out the price breakdown, especially if the price is out of sync with similar homes in the area.
8 | Scout the neighborhood with Google Maps
So, this is the exhausting part of me - I REALLY like to see the full picture. But it is soooo helpful.
Go into Google Street View and check proximity to restaurants, grocery stores, public transportation, and attractions you plan to visit. Look for potential issues like construction zones, industrial areas, or safety concerns.
It seems to me that often, these rentals are in areas that are “up and coming.” It doesn’t mean the area is dangerous, but maybe on its way back. Only you can decide how you feel about that. Just know that even though the little cottage with a front porch swing and pink door is screaming “Instagram Me!” the surrounding area might not match up.
Real story: I was looking at a place in great part of Charleston. This house was ADORABLE. The reviews were fabulous. The outdoor space had string lights and an egg chair, throws, etc. It had great reviews. But a couple of comments in the reviews made me wonder about the specific area.
In one of the photos, I could see the house number. I then looked at the Airbnb map, and saw the closet streets. Let’s say the house number was 612 and the surrounding streets were Becker, Greene, and Duke. I Googled 612 Becker, then 612 Greene, etc.
This doesn’t always work, but with some patience, you can often find the exact house, which I did. Now, I know the house is close to the shops and restaurants, but based on what I saw, I would not be comfortable walking at night. The covered outdoor space, which in the listing appeared to be in the backyard, is actually an open carport and you either see the car in the driveway, or the depressing street. It was also next to a commercial building.
This is why your intention is so important. If I was out all day exploring Charleston (like most people who visit), this might not bother me at all. But, I was going to be sitting in that adorable outdoor space carport working all day, trying to find inspiration and new ideas. Thus, it wouldn’t work.
9 - Travel with optimism!
And sometimes, even with all of this pre-work, it’s not like I thought it would be. But, any time this has happened, it almost always turned out that I was there for a reason. Maybe I find a hidden nook that has just the right vibe, or didn’t realize there was a dog next door that wanted to hang out with me while I worked, or that the sunrise was perfection from the front porch.
Most hosts genuinely want to provide a great experience. Focus on finding a place that meets your needs rather than chasing perfection. When you do book, communicate clearly with your host and approach any minor issues with understanding and flexibility. You may find that “meeting” the host is the best part of the property.
