Ask Amy: When friends snag your favorite vacation rental without warning

Dear Amy: For over a decade my family and another very close family of friends, “The Smiths,” have vacationed together on our favorite island off the Southern coast.

Our children view them as family and adore the parents and their children (who are exactly the same age as ours).

The Smiths are much more affluent than we, and owned their own home on the island for many years while we rented a house nearby.

Last year they sold their home (for an enormous profit, I might add), so now they must also rent a home for our beloved trip.

Imagine our surprise when we learned this year that they booked the very same rental house we have used for several years for themselves.

This is incredibly hurtful, but especially because we have been in a very tumultuous financial situation and depended on the significant “repeat renter discount” we received from the unit owners to rent their home.

While we obviously understand that we have zero right to control a rental unit, we are extremely sad and frankly heartbroken that our friends seemed to have no sense of this possibly being hurtful or undermining toward us.

We are unsure of how to move forward.

Should we say something about our hurt feelings just to clear the air?

Should we say nothing and take the hint that maybe they don’t feel the same way toward us as we do about them and not go on the trip this year?

Or should we just act like nothing’s wrong and pay for a more expensive rental and let it go?

– Sad and Confused in CT

Dear Sad and Confused: It is almost impossible to imagine that these savvy homeowners on a vacation island are unaware of how attached annual renters become to their usual rental property. Regular renters are often prized by landlords, who offer discounts to good and reliable annual tenants as both rewards and incentives. Oftentimes, landlords will give their “regulars” a right of first refusal before they open up their property to new tenants; I wonder why your landlord didn’t do this for you.

So yes, “The Smiths’” choice to snap up this rental for themselves leaves you scrambling (choice island rentals often book up many months in advance of the season).

You could respond to this by saying, quite frankly, “You guys snapped up the house we’ve been renting, and now we’re scrambling to find a new rental for our time on the island. I’m not sure we’ll be able to find a place we can afford, so if you know of anything, please let us know. We’re going to have to leave our plans up in the air for now. This is a bummer for us, and we’re all disappointed.”

(You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)