Family Vacation in Islamorada: Florida Keys with Kids

My parents visit Islamorada (village of islands) in the Florida Keys almost every year in the late winter.  With a baby in tow, 2018 seemed like the perfect year for a relaxing family vacation.  While the other trips with our son were either spontaneous or were tied to weddings (including baby’s first trip to Omaha, Nebraska) this was the first “real” vacation we had planned as a family. The warm weather all year round, the clear blue water, and the laid back vibe makes Islamorada, Florida the perfect spot for a family vacation.

islamorada beach

If you’re visiting Islamorada with little ones, be sure to also check out our tips for the beach with a baby.

How to Get to Islamorada

There aren’t any major airports in the northern part of the Florida Keys. The quickest and most cost effective option is to fly in and out of either Fort Lauderdale or Miami International Airport.  We flew into Fort Lauderdale-Hollywood International Airport since Southwest Airlines flies there. I also find it much easier to navigate Ft Lauderdale’s airport and quickly access the highway.  We rented a car and drove about 2 hours south to get to Islamorada, which is just past Key Largo.

Islamorada Florida with kids

Where to Stay in Islamorada

I love Islamorada for a relaxing, family vacation and definitely recommend getting a rental home through AirBnB or HomeAway.  Unfortunately, with Hurricane Irma hitting before our stay, the first two rental properties we booked were in pretty bad shape. The third property we found within our price range ended up working out perfectly. It had the 5 bedrooms and heated pool that we were looking for.  We loved the outside area with the in-ground pool, covered patio and dock along the water. (And we really could have spent all day every day outside at the house!)

Tips for Renting a Home in Islamorada

This might be obvious to most people, but be sure to ask about stairs (inside and outside) and fencing around the pool when renting a house with small children.  We discovered after arriving that the house was a little unsafe for kids with a steep spiral staircase inside and lack of fence between the back of the pool area and inlet.  This was the first time we ran into this issue- lesson learned!

Also keep in mind that many rentals in the Florida Keys are monthly, especially during winter months.  With a limited inventory of weekly rentals, I’d recommend booking early to make sure you have the most options within your price range.  If you’re looking for more of a resort setting in Islamorada,  Mooring’s Village is supposed to be a great a higher-end option and Drop Anchor Resort has more reasonably priced accommodations. I haven’t personally stayed at either resort, but both have a reputation for being family-friendly.

islamorada florida rental house

What to Do in Islamorada

With Islamorada being almost completely surrounded by water, there’s no shortage of marine life and water activities. Whether you’re visiting Islamorada with kids or without, you’re sure to find something there for everyone on your family vacation in the Keys. The laid-back feel in Islamorada also makes it a great place to sit along the water with a drink in hand and nothing to do but relax.


If you have slightly older children, deep sea fishing is the biggest draw to Islamorada.  The guys went offshore fishing one day and had a great time with Captain Larry Wren with First Choice Charters at Whale Harbor Marina.  While they didn’t catch the sailfish they initially went out for, they had a great day and caught wahoo, red snapper and king mackerel.

Fishing in Islamorada

Walk with the Manatees

 Islamorada is known for the manatees that inhabit its many inlets and waterways.  One of our favorite things to do was to go for walks in the morning and search for the manatees. On the left you can see how close they came up to the dock in back of our house, and we spotted several walking in the neighboring streets.

Theater of the Sea

Theater of the Sea is one of the main attractions in Islamorada, and it’s primarily made up of a few rotating marine life shows throughout the day.  We saw the dolphin show first and my 3-year old niece, along a few other kiddos, was chosen to feed the dolphins.  Our family also loved the sea lion show- especially our 10-month old son. The look on his face when the sea lions were doing tricks was priceless!

Following the shows, there’s a short bottomless boat tour that goes around the property and offers a little more insight into Theater of the Sea’s conservation efforts. We also participated in a reptile walk where we learned more about the rescued sea turtles that resided there.  

In total, we took about 2.5 hours to see the shows and walk around. Theater of the Seas also offers some fun extras like painting or swimming with sea lions or dolphins.  We didn’t do any of the animal experiences this time, but definitely will consider it in the future when the kids are older.

Robbie’s Islamorada

Many people know Robbie’s for the tarpon (fish) feeding. You can purchase bait for a small fee to feed the fish on the docks. Getting it to them before one of the nearby pelicans tries to snatch it from you is almost a game in itself. I didn’t get too close since I had my son in the stroller, but my niece and my brother loved it.  There’s also an open air market with several local vendors for handmade souvenirs and paintings. It’s definitely a great option if you’re looking for a locally made souvenir. There’s also a restaurant onsite, which is perfect for a drink outside at the bar with live music playing in the background.

Pelicans Tarpon Fish Robbie's Islamorada FL

Visit One of Many Parks in Islamorada

Islamorada offers several public parks with trails, picnic tables and play structures. Unfortunately Anne’s Beach, once a beautiful public beach, is still closed from Hurricane Irma. Many rental properties and resorts in Islamorada are either beachfront or have access to a private beach. If going to the beach is important to you, be sure to look for a property in Islamorada with access to a beach.

Day Trip or Overnight Trip to Key West

Key West is just about a 2-hour drive from Islamorada, so it’s totally doable for a day or quick overnight trip.  We were fortunate enough to have the grandparents babysit overnight for a kid-free dinner and night out. (Which, let’s face it, we could barely stay up past 11pm.)  

We stayed at the La Concha Hotel & Spa; a boutique hotel right in the heart of Key West.  The rooms were beautifully decorated and the on-site facilities including the pool and the central location were perfect. I would definitely stay there again.  For dinner that night we were craving sushi and had a yummy dinner at Mangoes Key West and went to a few bars before before ending the night with an amazingly huge and yummy cookie sundae right across from our hotel at Mattheessens Key West.  

The grandparents drove the kiddos down the next day and we visited the Key West Butterfly & Nature Conservatory.   The look on my son’s face when seeing butterflies come right up to him for the first time was priceless. While the conservatory was small it was jam-packed with beautiful plants, birds and butterflies.  We also took the requisite photo op at the Southernmost Point and spent time aimlessly walking around to take in the scenes in Key West.

Where to Eat in Islamorada

We made a lot of family meals at home while in Islamorada, but there are so many great places to eat. We’re always a fan of looking for outdoor places at warm weather destinations, and it’s a bonus if they have live music! Below are a few of our favorites for laid-back family dining.

Lazy Dayz

Lazy Dayz is of the most popular restaurants in Islamorada and a great choice for our first night out.  The restaurant has a huge menu with a ton of fresh seafood options. The restaurant has ample space with a number of indoor/ outdoor seating areas. Lazy Dayz is also a great place to catch live music right on the beach.

lazy dayz islamorada

Lorelei Restaurant & Cabana Bar

We went to Lorelei’s for breakfast with the kiddos when the guys were out fishing one morning.  We were looking for a casual waterfront spot and it was exactly what we wanted.  The restaurant is probably known more for it’s happy hour than it’s breakfast. That said, the breakfast was still great, the service was quick, and the kids loved all the birds and fish by the water.

Lorelei's Islamorada Florida

Midway Cafe

We stopped at Midway Cafe in need of a quick caffeine fix one day. Midway is known for serving the original key lime pie. (The “real” kind with merengue on top.) In addition to the key lime, the restaurant has a great selection of breakfast, baked goods and specialty coffee drinks.  The decor is bright and cute, the service was great and everything I saw coming out looked yummy. Shoutout to the owner who made all 6 of our lattes with a hand espresso press!

Morada Bay Beach Cafe

If you’re looking for a classy outdoor cafe, Morada Bay Beach Cafe is a great lunch spot right on the beach. I had the Beach Cafe Salad with ahi tuna that was super fresh and the Ketel Beachside to drink.  This place is also known for their monthly adults only full moon party right on the beach, and it’s a filming spot for the TV show Bloodlines.

Islamorada water

Islamorada Fishing Company

The waterfront setting and live music was my favorite thing about the Islamorada Fish Company. We ate there one night to take advantage of the fresh fish preparation after a day of fishing. Since Islamorada is known as a fishing town, many of the restaurants let you bring your own fish. They will then prepare it and serve it family style with sides of your choice.  (A great option if you want someone else to do the work but still have the satisfaction of eating the fish you just caught!) The Islamorada Fish Company is also connected to the Bass Pro Shop, which was an attraction in itself.

islamorada fishing company

Have you been to Islamorada? Please share if you have anything to add in the comments!

*Our trip took place in March 2018, several months after hurricane Irma hit. I was saddened to see that so many towns, attractions and homes were still in shambles.  One of the many benefits of tourism is that it boosts the economy, especially in a time of need. If you can’t visit the Keys anytime soon, consider donating to one of the charities listed here

Islamorada Florida with kids

Will’s Trip Stats:  Islamorada & Key West, Florida // March 2018 // 10 Months Old

Children’s Book Inspiration: Deep Deep Sea by Frann Preston-Gannon

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