On Being the Family’s Travel Agent

The time of year has arrived when I drive myself absolutely insane looking for our family’s annual vacation house. (cue the fanfare!)

Next year will be our 13th year (lucky 13?) of vacation houses, and each one has been better than the last one. No pressure.

Over the last two years, finding a vacation home is proving to be very challenging (Thank you, COVID!). People are sticking closer to home, opting for driving destinations vs flying. And because our vacation house geographical area is New England, more than 70% of the houses are already booked for next summer. Not only are they booked, but the prices per night have gone WAY up.

I know about this price increase because I have been stalking houses for so long, and have made so many Trip Boards and Wish Lists that I remember how much houses cost. Houses that were in my “acceptable” price range last year, have increased more than $200-$300/night.

As the family’s travel agent – and someone who has traveled extensively with both my parents and my inlaws – I have a very good idea of the type of house that will work for us as a group.

Criteria includes:

• 4+ bedrooms
• Ideally, 3+ bathroom (one for each family; we could get away with 2, but…why? we’re on vacation)
• Close to beach (bonus if it’s walkable!)
• At least 3,000 square feet (trust me, this is a good starting point for square footage)
• Parking for 3 cars
• Close to a town with great restaurants
• Large kitchen, big enough to fit the entire family around the island and leave me enough room to move around and cook
• Countertop where we can set up our bar
• Seating for 8 in the living room; we need to all be able to be in the living room relaxing at the same time
• Outdoor space for eating and hanging out
• A reading nook for my mom
• A desk area for my mother in law to do her “correspondence”
• A chair where my dad can go from reading to napping in 3 minutes flat
• A play area for Little Mister
• An outdoor napping space for Mr. KK
• A warm spot in the sun for me
• With our price range (which, it seems, used to be easier than it currently is)

I do all of my research on two specific websites; one rhymes with Bear B and B and the other, Mer-bo. I have spend so many hours on these two particular sites, that I have grown to know each and every house for rent.

My obsession is SO extreme, that you could show me just the fabric swatch of a sofa cushion from a random house and I could likely tell you what the house looked like (“It’s the modern farmhouse with the wide plank floors, blue kitchen cabinets and orange drapes”) where it was located (“Thats the house in Kennebunkport, near the beach with the playground in the good walking neighborhood with the ice cream shop you can walk to”); whether or not it was in our price range (“Affordable before 4th of July but is over $1500/night in August”) and one other random yet distinguishing fact about the house, such as (“Oh that’s the place with the finished basement with the dart board and pool table and weird light up Nude Beach sign”)

While this year is proving to be challenging, it hasn’t stopped me from obsession over these two websites. I’m on them late at night when I can’t sleep, and I’m back searching first thing when I wake up.

If I may make a suggestion to the creators of these two websites: can you please create a “thumbs down” icon? I already have the option to “favorite” a property with a little heart, but I would also like to be able to mark any houses I’ve looked at and rejected so that they no longer show up in my search results. There is nothing more annoying than having a house show up in search results, tricking you into looking at the property again until 4 photos in you realize you’ve already looked at the house and dismissed it for whatever reason.

And speaking of rejecting properties, it doesn’t take much for me to say “no” to the house (sorry, home owners). I rationalize it as if I’m going to spend a precious week of vacation somewhere, it better be pretty spectacular.

Reasons why I will reject a property almost immediately (don’t hate me):

• Outdated kitchen
• Outdated living room
• Outdated anything
• Patio furniture acting as actual living room furniture
• Carpet in the main living areas (I’m sorry, but carpet in beach houses is weird)
• Black leather couches
• Dark wood paneling
• No AC
• Shared outdoor space with owners
• Too many personal items in the house (Are you living here, or am I?)
• Cluttered countertops and dressers
• Raised ranches
• No outdoor space
• No linens included
• Blonde wood furniture
• Non-open concept floor plans
• Mismatched furniture (but not in a cool way)
• Four poster beds
• Papasan chairs
• Big furniture in a small room
• Small furniture in a big room
• Doilies

Before you judge please know that I believe if you are going to be charging $1,000/night to rent your house, ti better well be worth $1,000 a night. And white appliances in the kitchen are not worth that much money.

But here’s a secret, homeowners: your photos can tell a really nice story. If you take nice photos.

What I would say to the people taking the photos for house rental listings:

• Put the toilet seat down
• Wait until a sunny day to take photos; natural light trumps evening with the lights on every time
• Put the dishes in the drying rack in the kitchen away
• Toss the magnets on the fridge
• Make the bed vs “pulling up the comforter” (hello, hospital corners!)
• Wash your windows, fixed broken outdoor furniture and pick up your child’s toys in the yard
• How in God’s name are your photos blurry???
• If your finger is in the photo, take a new one. Please.
• If you can’t get a good photo of the entire room, just forget it. No one needs to see a close up of bi-fold closet doors

Do a better job, people!

Fingers crossed I find us a family rental!