What is the Best Key for Families? See Where We Stayed and What We Loved!

I love to see all sorts of landscapes, but my absolute favorite is sparkling turquoise waters. Pair that with an amazing beach resort and I am one happy girl! I’ve been eyeing a resort in Key Largo for a while and we had some free night certificates to use, so I started planning!

With a mix of budget-friendly stays, credit card points, and a few splurges, we were able to create a family vacation that was fun, affordable, and full of adventure.

Pittsburgh to Miami

We typically fly out of Pittsburgh or Cleveland, but we prefer Pittsburgh for a few reasons.  First, there is a Hyatt Place near the airport that is a great option for early morning flights – and can be booked for around 8k points.  Plus, we use Fast Park to park our car, which is about half the price of what we pay in Cleveland with the same company.  And lastly, the Pittsburgh Club Lounge is larger and offers a better selection of food than Cleveland’s Club Lounge.

Using Points & Miles really allows us to stretch our budget, meaning we can either splurge a little more on our trips or take more trips throughout the year.  We found flights on Southwest using points, which saved us a large chunk of money on this trip.  Plus, we have TWO Companion Passes this year, which means two of our flights are free.  We only had to pay the taxes and fees, which cost our family a whopping $56 for our round-trip tickets! You can see how we earned our Companion Passes here. 

We’ve had at least one of our Companion passes since January 2024 and have flown round-trip to Hawaii, Minnesota, South Carolina, Texas, Florida (Orlando), Louisiana, New Mexico (one-way), Las Vegas (one-way), Florida (Miami) and Idaho. For each of these trips, we used the Southwest points we earned from credit card welcome offers and our companion passes, paying no more than $56 for these round-trip flights. We would never have been able to take the amount of trips we have without points!

Food, flights, activities and accommodations are the biggest expenses on our trips so anytime we can save in any of those categories, it certainly helps! One of our favorite credit card perks is accessing airport lounges. Airport food is expensive, so having lounge access saves our family at least $50.  Most lounges offer a variety of food, drinks and even alcohol so we can fuel up before our flights and even on our layovers! Not all lounges are created equal though, so some are definitely better than others. Unfortunately, our favorite card with this lounge perk is changing in early 2026 so we’ll have to re-think our strategy for family lounge access next year.

On this trip, we took advantage of the lounge in Pittsburgh and then in St. Louis for our layover.  This saved us on needing to purchase breakfast, so when we landed in Miami, we were ready for lunch.

A Stop at Biscayne National Park

On the way out of Miami, we made a quick stop at Biscayne National Park. We visited the Mighty 5 National Parks in Utah a few years ago and since then, we try to hit the National Parks in every area we visit. They offer some pretty cool sights. And even at a park where the water is the park, there are still cool things to see in the Visitor Center.

The Visitor Center was a nice introduction, and a short trail nearby gave us the first taste of that salty air and coastal calm. Two of my boys play the trumpet in band (and my husband did too) so the park Ranger had them blowing in conch shells. It took a little practice, but they got it!

First Night in Key Largo

Our first night was at the Hampton Inn Key Largo, a no-frills but solid budget option hotel. Thanks to a hotel credit from our Hilton Surpass Cards, we saved $100 on the stay (making our cost around $75 for the night). The kids loved fishing off the dock (rods were available to rent) and swimming in the pool, while we relaxed with drinks from the tiki bar. Breakfast was classic Hampton — plenty of hot and cold options to keep everyone happy. 

Although this hotel is a older, it really gives a resort feel with its small beach and tiki bar.  If you’re on a budget, this is truly a great option, and we would happily stay here again!

Driving the Overseas Highway

The next morning, we hit the road toward Key West. The Overseas Highway is a road trip dream: endless ocean views, turquoise waters, and plenty of quirky roadside stops.

A true highlight was Robbie’s of Islamorada, where the kids fed giant tarpon leaping out of the water. It’s touristy, yes, but in the best way — lively, colorful, and fun. There were so many quirky photo spots and plenty of merchandise.

It did cost $2.50 just to enter the docks where you feed the tarpon, plus another $5 for each bucket of about 5-6 fish. The kids loved it though so I wouldn’t hesitate to splurge again if we went back to the Keys.

We tried to time our drive just right so we’d end up at Sunset Grill and Raw Bar for lunch. It was a great stop too, especially since our son, Cohen, was thrilled to finally get sushi (and he raved about the 7-mile roll)!

Key West: Exploring the Island

By afternoon, we arrived at our hotel, the Best Western Hibiscus Hotel. It wasn’t fancy, but it ticked every box: clean, free breakfast, free parking, a nice pool, and a prime location — just a five-minute walk to the Southernmost Point Buoy and about 15 minutes to Mallory Square. We didn’t use points on this hotel, but at $208/night, it was a total steal for Key West!

That first evening we wandered Duval Street, stopping at Kermit’s Key West Key Lime Shoppe for the famous chocolate-dipped frozen key lime pie on a stick (plus samples of cookies, nuts, crackers and more). Later, we grabbed dinner and headed to Mallory Square for the sunset celebration. Unfortunately, clouds spoiled the sunset, but the performers and vendors were fun to see.

On the way back, we popped into Banana Cafe for late-night crepes. We grabbed them to go, but I have to mention the wonderful service at this restaurant. I placed a carry out order, but they offered me a place to sit as well as a drink. It’s definitely something to mention when you get great customer service. And the banana Nutella crepes we got disappeared in minutes!

The next day started with breakfast at the hotel before checking out a few sights: Mile Marker One, some shopping, and a walk past the Hemingway Home. Lunch was at Hogfish Bar and Grill where the seafood was outstanding (and even the cheeseburger and tacos were great for non-seafood eaters like me).

On our last morning in Key West, we finally braved the line for the Southernmost Point Buoy. Pro tip: go on a day when there are no cruise ships in port or early in the morning — the wait was much shorter than mid-day. We walked by mid-morning, mid-day and before sunset and the line was so insane!

Our Honest Take on Key West

While we were glad to see Key West, it wasn’t our favorite. The beaches weren’t great for swimming, and the smell near the water was pretty rough. If nightlife and bar-hopping are your scene, you’d probably enjoy it more, but with kids, we found it a bit overrated. I would have loved to get out to Dry Tortugas National Park, but we just didn’t have the time on this trip.

Heading Back North: Islamorada & Key Largo

On the way back up to Key Largo, we stopped at Bud N’ Mary’s Marina to feed more tarpon. It was quieter than Robbie’s, but Robbie’s had the more exciting vibe. You didn’t have to pay just to go on the docks, but the buckets of fish were about the same price.

Lunch was casual, and then we found a gem: the Islamorada Brewery & Distillery. This place was perfect for families — we enjoyed flights while the kids played giant Legos, cornhole, and outdoor games. Because it was a brewery and distillery it was a perfect compromise.  While my husband loves all sorts of beers, I am not a fan.  However, I really enjoyed their their key lime colada and rum punch!

We also checked out Rain Barrel Village and grabbed a photo op with Betsy, the giant lobster! There are a variety of shops that we also checked out while we were here.

We then stopped at the Blond Giraffe Key Lime Pie Factory. Their whipped cream-topped pie was my favorite key lime dessert of the whole trip.  It was so smooth with just the right amount of tart key lime flavor.  And the whipped cream, for me, added that extra punch of sweet to every bite! I highly suggest a stop if you’re in the area!

A Slice of Luxury: Baker’s Cay Resort

Our next two nights were spent at Baker’s Cay Resort in Key Largo, a luxury Hilton property. We used our Hilton Surpass free night certificates here, which made this splurge possible. At close to $700/night, this isn’t a place we’d typically visit on our budget, so getting to enjoy it for free was exactly why we LOVE earning and using points and miles!

On top of getting our room for free, our Hilton Gold status gave us daily food and beverage credits ($36/night) — another budget win! It’s like Hilton PAID US to stay here! You can read all about how we earn these awesome free night certificates here!

The resort was a dream for families: pools, a lagoon with paddleboards and kayaks, floating docks, fishing rods (free in the mornings), sunset ceremonies with champagne and s’mores, foam parties, crafts, and even a pineapple scavenger hunt. We were also upgraded to a water view room, which made the stay even more special.

We would absolutely come back to this hotel! The staff was phenomenal – from check in to check out! When we checked in, the bell hop greeted us and gave our kids a popcicle and the staff for the kid’s activities were also wonderful! The water here was also so much nicer than Key West and did not have the smell we encountered in Key West!

Besides all of the water activities, there were also bike rentals, pool table, gigantic Scrabble board, cornhole, volleyball and ping pong. Our older two kids loved being able to roam the resort on their own and enjoy these included amenities!

The resort also had pool games, a foam party and crafts that were all included with your stay. Even with the higher price tag, the amenities really does help offset that cost if you are paying with cash.

If there was one place we’d recommend for dinner in Key Largo, it’d be The Fish House. If you’re looking for fresh and amazing seafood, this is THE spot to go! There aren’t a ton of options for those who aren’t seafood fans, but you’ll find a few things. And the hushpuppies – OMG – they were so freaking good! Nothing like the ones we are used to here in Ohio from fast food restaurants. These were sweet with a honey butter. I could have eaten a basket of them on my own!

Wrapping Up in Miami

For our final night, we stayed at the Hilton Miami Airport Blue Lagoon before our early flight. The hotel welcomed us with drinks and empanadas, and our Hilton Gold perks gave us extra food credits ($30 for the night) — a nice way to end the trip. In addition, our Hilton Surpass Credit Cards saved us an extra $100 on our hotel stay too, leaving us to pay only $50 for the night. The only disappointment was the pool area, with a cold hot tub and poor towel service.

Final Thoughts

Overall, our Keys adventure was fun, but our hearts leaned more toward Key Largo than Key West. The activities, resorts, and family-friendly vibe in Key Largo made it the highlight of the trip. Key West was worth seeing once, but probably not a repeat for us. If you’re after beautiful beaches, Florida has better options — but for quirky roadside stops, key lime pie tastings, and unforgettable family memories, the Keys still delivered.

Have you been to the Keys? What have been your favorite stops?