Florida Keys on a Budget

how to travel the florida keys on a budget

As I looked at our upcoming summer I realized we had a summer vacation planned for just Jake and myself, one with my family but none as a family of three. Jake was in the middle of crazy, crazy work weeks that were making it difficult to spend time together as a family. And me–well I always love trying to find a good bargain on flights. So after convincing Jake to take a couple days off, I found some dirt cheap Florida tickets from a new airline here in Pittsburgh called Allegiant. We booked a car and two hotels and I began counting down the days!

how to travel the florida keys on a budget

We had kept a mental bucket list of traveling in the back of our minds for a while and on the list was Florida Keys Road Trip. Jake had done it with his father years ago but we wanted to do it together. So that’s what we did. I prayed Emmett, our 1 year old, would sleep well and we didn’t make any real plans other than seeing my friend from college the night we got down there.

florida keys on a budget

It ended up being such a fun weekend. It was great catching up with my friend and Emmett slept like a baby in the backseat as we drove the Key West Highway. We actually ended up with an upgrade for our car at the airport thanks to a nice worker who said he noticed we had a child and wanted to help us out. They bumped us up to a car with air conditioned seats and other fun upgrades, but I just really cared about those seats. 😉


Day 1: We flew down to Fort Lauderdale. Allegiant Air had some wonderful deals connecting Pittsburgh and Fort Lauderdale. It forced us to pack lightly but we ended up with everything we needed. We picked up a rental car at the airport and headed to the La Quinta. We chose this hotel because of the fact that is 1) a nice hotel, 2) cost effective and 3) includes a decent breakfast. Emmett had a bunch of diet restrictions at the time and we were able to find him food there.  It was also in close proximity to the friends we were visiting.

Day 2: We hopped in the rental car and drove the Overseas Highway. It took us the whole day, but we stopped for lunch and drinks, found a little swimming spot and ended up at the Hemingway Home soon after it closed at the end of the day. We found a local spot to eat and then headed to the southernmost point in the continental U.S.A. Since Key West itself is pricey to stay in, we drove up a couple of the keys and stayed on Marathon at The Tropical Cottages.

Day 3: We found a beach not too far from our cottage called Sombrero Beach. It was absolutely beautiful. We drove the rest of the way back and stopped in Miami for the evening.  We found another beach, got some great dinner and stayed our last night back at the La Quinta.

Day 4: Travel back home!

Where to stay:

As I mentioned in our itinerary, we stayed at two places: La Quinta and The Tropical Cottages. The Tropical Cottages are actually ON the Keys though. We found the Tropical Cottages through a google search and chose it because of its price point. It also gave us more room than the typical hotel. We had two rooms, a bedroom and a living room/kitchen area. We were able to set up Emmett’s pack n’ play in the living room while we took the bedroom.

The place was super low-key which gave the Keys their island feel. The owners left our cottage key with someone in the outdoor common area because we were arriving later at night. We had a porch that we hung out on after Emmett fell asleep and it was so relaxing.

The location was great because Sombrero Beach was nearby and was super accessible. There was also a little road we could walk down to see some water behind the cottages.  If you like a laid back vacation, I would definitely recommend these cottages.

Photo Diary


(Key West!)

 (the Hemingway Home!)

(Southernmost Point of the Continental U.S.A.)

 (our second hotel was a little cottage!)

(Sombrero Beach Marathon, FL)

(North Beach in Miami)

Even though our trip went by quickly, we had so much fun without much of an agenda. It is totally doable to go to places in this country that might be deemed “expensive” and find alternative ways of doing it. We just drove where we wanted to and knew we had hotels to arrive at once we were done driving. It was fun to see the Florida Keys and cross something off of my bucket list. Even thought Emmett was young and won’t necessarily remember this trip, I have these pictures to show him someday!

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