Beach Vacations

Family Dream Vacation in Key West

This post is sponsored by HomeAway, offering the largest selection of worldwide vacation home rentals online.

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.


Key West Florida Sunset
Photo courtesy of WayneConcepts on Flickr

Growing Bigger & Wiser

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.

Room to Breathe

We’ve had great success renting apartments around the world. A stunning summer week in a quintessential Paris apartment, a long winter weekend in Edinburgh, Scotland (we needed extra room for all our coats and scarves) and a Spring Break in Disney dominated Orlando. On each trip, our home away from home added to the enjoyment and success of each trip.

Dream Digs

Which only leads me imagine, dream actually, what it would be like to rent a house for a special family trip.  Not just an ordinary house, the kind of house you dream about. The kind of house that WOWs you and makes you feel good the moment you walk in the door.

Location, Location, Location

For me, a dream rental vacation home is one where you can see warm, turquoise water from every window. A home where you can count the steps from your bed to the beach on two hands. A home where you can escape it all, but quickly make it back when your taste for modern comfort, adventure or simply incredible fudge kicks in. Chocoholics stay tuned!

Key West

I’d love to spend a week with my family at a dream rental home in Key West. Surprised? Don’t be. Though many think of the island as an adult destination, there’s plenty for families to enjoy.

Key West is a fun, seaside cottage style town for all ages to explore. Where much of Florida can look shiny and new, Key West takes pride in its unique look and vibe. It’s a place that likes to party when the sun sets, but in my experience the party rages on in a way that revelers and families can enjoy together. I spent a couple days in Key West with my teen daughter in December. Not enough to learn all its in and outs, but long enough to decide it’s a place I’d love to take the entire family.

Looks Mean (Almost) Everything in  My Dream Rental Home

No two homes in Key West are exactly alike. My dream rental home would be brightly painted with a palette of colors that would raise eyebrows on my block at home. It would have three bedrooms, one for mom and dad, and one for each of the kids. Three full bathrooms; yes we’ve been practicing sharing since kindergarten, but everyone deserves a week off.

The kitchen should be sparkling and spacious with tons of natural light. Stainless steel, top of the line appliances please. Not that I’m planning on cooking every meal, but preparing seafood fresh from the water is a tasty and fun way to spend an evening when the whole family can and wants to fit into the kitchen. It has all the makings of a comical pilot for the Food Network. I doubt we’d even set a formal table. With plates in hand, the beach has the best seat in town.

The fridge would be stocked with fresh squeezed oj and the requisite family breakfast basics. But running out of milk would be ok too. I can’t think of a better way to start your day than an early morning stroll or jog on Key West. Pick up some fresh baked muffins or pastries and help the kids hunt for the islands seemingly thousands of roosters that roam the seaside roost. Getting up early is no big deal when you know taking an afternoon nap in your dream rental house’s master bedroom is an option on the day’s itinerary.

Though the beach and warm water would pull my family like a magnet, a pool and even hot tub at the house would be lovely. And of course an outside shower. No one likes walking on sandy floors.

Six Toed Cat Hemingway House Florida USA
Six Toed Cat

Learn About a Legend

I like to sneak a little learning in our family vacations. A trip to the Hemingway Home and Museum fulfills that requirement. The kids will learn about the famous author, but my guess is the 44 six-toed cats that currently call the Hemingway House home will be the highlight.

Evening Entertainment

Though I’m sure the entertainment system in the house would be state of the art, we might not even need a television in the house. (My husband will no doubt disagree when he reads this). Once you’ve watched the sunset from Mallory Square, it will be hard to keep from going back night after night.

After the sun sinks into the sea, street performers come to life, entertaining crowds of visitors and locals. Artists load tables with wares like paintings and hand woven baskets. My daughter fell in love with a bracelet made by local dad and artist Matthew Boa. When it was to small, her disappointment was short-lived. He custom made another in what seemed record time, while teaching her a few things about beads and gemstones along the way. We made it to a late dinner, eventually.

Room for Dessert

An after dinner stroll is a must, whether dinner was in a restaurant or my dream rental house kitchen. And if we’d happen to wander near Mattheessen’s and come home with some freshly made fudge or ice cream, that would qualify as a successful day. No worries when my youngest gets chocolate everywhere, there’s a washer and dryer at the house.

Now, that I’ve thought this all out.. What am I waiting for? Spring Break is right around the corner.

Brought to you by HomeAway, offering the world’s largest selection of vacation home rentals that provide travelers with memorable vacation experiences and benefits, including more room to relax and added privacy, for less than the cost of traditional hotel accommodations.  Make memories where you stay, not just where you go. – let’s stay together.

Start a Discussion

  • Wow, That is a Beautifully put story about staying in the Keys.
    My Husband grew up in St. Augustine, Fl. Moved up to Massachusetts and always regrets never making the trip to see the Florida Keys.
    I too being his wife now would love to go with him.
    Both are children are gone from the “nest” and It’s our time to travel.. This is surely one of the places we would love to see. ” Florida Keys!!!

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