I’ve been researching vacation rental websites for my parents who have been wanting to come up and visit, however I want to put them into a nice location where they’re not trapped in some interstate exit world with just a gas station and a couple restaurants nearby. So I’ve been jumping on the web trying to find some nice places where they might be able to lounge around peacefully but also could easily walk within 5 minutes to a picturesque downtown like Rockport or Salem.
I’m not demanding in terms of actual location. Just the "North Shore" pretty much would suffice, although I’d be open to Concord or other nice inland towns. However, I’m more particular about the actual local "amenities" mentioned above of the location rather than where in the world the location is. So for someone like me, a map with locations would be the most useful solution and provide the best user experience. I could see where all the towns are, like Manchester-by-the-Sea as well as Gloucester and Rockport, all at once, and I could check out all the little dots in and around those towns which would be homes and apartments available for rent.
Unfortunately, very few websites allow you to view by a map. They force you to drill down deeper and deeper and choose actual cities, like this otherwise well-designed website at Vacationrentals.com. This is just time consuming.

I’ve never really understood this mentality when it comes to the information design of most Vacation Rental sites in general. That goes for any property rental or even real estate site. A lot of people would rather just view a map, and compare the properties to each other. If you think about it, someone who is looking for a vacation rental, or looking to move somewhere, is someone who most likely isn’t actually that familiar with the region. They have heard of Cape Cod, but have they heard of "The Berkshires"? We New Englanders have, but what about someone from Arizona? Visitors may have heard of Salem, but maybe they have never heard of Beverly, and have no idea it’s right across the river and might have exactly what they’re looking for if they can’t find it in Salem. How do they know they should click on the link for "Beverly"? Without a map, or previous knowledge, they have no idea.
By not providing a map, you are assuming that your visitors know where all those cities are or that they know exactly what cities they’re looking for. The truth is, a lot of people are like me, and they don’t care if they’re in Yarmouth or Sandwich… they just want to find a nice place in Cape Cod that is close this sort of geography, and that sort of activity and so on.
Any kind of property site — whether it’s vacation rental, apartments, condos, real estate, etc. — really should always have some kind of "view by map" function which allows the viewer to use an existing and robust mapping system (like Google, etc.) which features the actual locations of those properties across the map.

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