Six Toed Cat Hemingway House Florida USA

Family Dream Vacation in Key West

As my kids get older, our vacations are changing. Though my tween and teen are always up for a good adventure, time to relax and just hang out as a family is inching higher up on the wish list. The trick then becomes getting just the right balance. Too much down time can quickly turn into boredom.

As a family of four, we’re by no means a big family, but now that my girls are close to full grown size, being packed into a standard hotel room doesn’t quite hold the allure it once did. Necessary hotel accommodations can also be tough on a family budget.


Finding the Best Family-Friendly Vacation Rental

Villa, home, cabin, apartment and/or condo—where you go may change what it’s called and what it looks like—however, the process to find and rent independent accommodations for family vacations is the same.

There are two main sources on the Web for rental inventory: 1) direct-from-owner-sites like VRBO/HomesAway/ (the list of options is exploding) and 2) rental agencies who facilitate rentals and services on behalf of the owner.


How to Rent a Vacation Home with Friends and Stay Friends

The title of this post is a bit misleading because it implies that every friend is a good candidate for sharing a vacation home. I’d argue this is not the case—just because you are great friends at home doesn’t mean you are a good match to share a rental.

When I organized villa rentals for families as part of our Italy trip planning service, there were several occasions when families didn’t get along on the road and it tarnished the vacation for everyone.