Planning a Florida Keys Family Vacation: Tips and Tools

Family strolling on a sandy beach in Florida Keys

The Florida Keys are home to the United States’ “only living coral barrier reef,” the country’s southernmost national park, beautiful 360-degree views of the Gulf of Mexico and Atlantic Ocean, and some of the best outdoor activities in the region. 

The archipelago is simply the perfect destination for a family of adventure-seekers, history buffs, foodies, or bon-vivants.

The Keys are a little slice of tropical paradise without the need for a passport (or four). Planning a family vacation to the Florida Keys is easier said than done, however, so we’ve put together some tips and tricks to ensure you make the most of your time in the Florida sun.

First Things First: Figure Out What You and Your Family Want.

The Florida Keys are a string of tropical islands stretching from roughly 15 miles south of Miami all the way down to the uninhabited Dry Tortugas National Park, 70 miles west of Key West and about 160 miles from Miami. 

Before you make any decisions, discuss what you’re looking for in a Keys vacation.

Ask your family and yourself the following questions:

  • What kind of vacation do you want? Sporty? Relaxed? Full of outdoor adventures or cultural explorations?
  • What is your budget?
  • What kinds of family-friendly activities would you like to do?
  • When and for how long would you like to go?

You also have travel options. Many major American cities fly direct to Key West, so you could choose to set up base there. However, the road trip from Miami to Key West takes about 3.5 hours and features a number of iconic stops along the way. 

Thankfully, the islands are close enough in proximity that you can hit them all without too much hassle. 


Where to Stay: The Best Family-Friendly Resorts

Now, just because you can easily get to different islands, doesn’t mean the hospitality choices are all equal. Luckily for you, there are plenty of resorts to accommodate the whole family with the kind of amenities the kiddos will love. Here are five you should check out before deciding where to check in. 

Isla Bella Beach Resort | Marathon

You’ll love Isla Bella Beach Resort for its fine dining options, stunning views of the ocean, and beach bar. Your kids will love its five pools, snorkeling, scavenger hunts, and more. Plus, this luxury stay is centrally located if you wish to explore the neighboring islands. 

Southernmost on the Beach | Key West 

The southernmost spot of the lower 48 gets you close to all the action and adventure Key West has to offer. Book excursions like a seaplane trip to Dry Tortugas or an eco tour of Key West. 

Hawks Cay Resort | Duck Key

A USA Today 10 Best Reader’s Choice family resort, Hawks Cay lives up its reputation with a wide range of aquatic adventures. Jump in the ocean with dolphins, or let the kids explore the pirate ship pool. 

Hampton Inn Key Largo | Key Largo

Stylish rooms, plenty of pool space, unique outdoor spaces...there’s nothing complicated about the Hampton Inn Key Largo, which makes for an ideal lowkey stay for all of Keys adventures. 

Glunz Ocean Beach Hotel | Marathon

Are grandma and grandpa joining in on the fun? Then Glunz Ocean Beach Hotel is the place for you. The beachfront villas are three bedroom, three bath, so you have a nice homey abode to return to each night. 

What to Do

Once you have lodging figured out, it’s time to fill out that itinerary. 

While the Keys are understandably known for their water sports—fishing, scuba diving, and snorkeling—there’s no shortage of activities you and your family can do while there. 

And don’t worry about cramming. You’ll mix in a variety of adventures even on an extended weekend, while leaving plenty of time for relaxation in the sun.

There’s world class snorkeling on Key West (such as at Fort Zachary Taylor Park), Key Largo (such as John Pennecamp Coral Reef State Park), and of course at the Tortugas.

History and culture buffs should read about the Hemingway House at Key West and the many polydactyl cats running around the grounds. You could even take a guided tour of Pigeon Key, just under Seven Mile Bridge, the home of an ill-fated over-water train project

If you and your family are foodies, spend ample time in Key West, where there’s no shortage of incredible seafood, world-class Cuban coffee and assorted pastries, and of course, all the key lime pie you could eat. 

But the fact of the matter is that there are great food spots all over the Keys, so it comes down to preference (apologies for the families of picky eaters) and budget. 

How to Score Deals

While the Florida Keys aren’t exactly Orlando-level pricey if you know where to look, it’s still a challenge to save money when you’re traveling with the whole family. In fact, you have to pour hours of time and effort into your research, and even then, there’s no guarantee.

Look for flight deals and even rarer mistake fares. Reach out to your preferred hotel to see if they can match or even beat the prices on third-party booking sites. (This is a tried-and-true method, as many hotels lose out when guests book through third-party websites.)

And when planning, be conscientious of where you’re going and what activities you’re doing. Key Largo, for instance, is considered one of the most affordable of the Florida Keys, so if you’re looking for paradise on a budget, your best bet is to start researching resorts there.

This process, however, is incredibly time-consuming, especially if you need to be budget-conscious. 

You’ll need to be quick-handed about booking flights at the right time, sweet as honey when trying to negotiate with proprietors, and clever about finding discount codes that aren’t easily available—it’s a headache. There’s a reason most travel agents cost a pretty penny.


Turn to an InteleTravel Advisor.

There’s an old joke about trip planning: If you go it on your own, it’s so overwhelming that sometimes you need a vacation from planning your vacation. 

So why not skip the stress and confusion of planning and logistics by tapping into InteleTravel’s expertise?

You can delegate all tasks and questions to an InteleTravel advisor, and the best part: It won’t cost you a dime to use our services. We don’t charge any money for our expert trip-planning services (rather, our advisors make money through their industry partnerships).

Plus, you get all the benefits of working with an actual person. They communicate to understand your preferences and can offer personal touches that will delight your family. They can help you settle those internal debates: Should you road trip from Miami or is it worth it to fly direct to Key West? What meals should you splurge on? 

Our advisors are rigorously trained and spend years building relationships throughout the industry. That means they’re prepared to research and design the vacation that you want—and they’ll even tap into their contacts to save you money that you’d be spending were you to book flights, hotels, and tours on your own.

Turning to an InteleTravel advisor means more time to enjoy yourself, while still giving your family the vacation of their dreams.

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