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 new baby, 2018 seemed like the perfect year for a relaxing family vacation.  The other trips with our son were either spontaneous or were tied to weddings (including our first trip with a baby to Omaha, Nebraska.)  This was the first “real” vacation we had planned, and we couldn’t have been more excited for a family vacation in Islamorada in the Florida Keys. The warm weather all year round, the clear blue water, and the laid back vibe makes Islamorada the perfect spot for a Florida vacation with kids.

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

Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

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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.

When you’re driving in the Florida Keys, you’ll notice that there are mile markers along the overseas highway. The mile markers in the Keys are an easy way to designate both location and distance. (In some cases you may just see a mile marker to designate location versus a physical address.) Islamorada is generally located from mile market 91 to mile marker 73. If you’re looking to do a road trip in the Florida Keys, the overseas highway is a beautiful drive regardless of where you’re starting and ending.

Private Beach Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

Vacation Rentals in Islamorada

I love Islamorada for a relaxing, family vacation and definitely recommend getting a rental home if you’re traveling with a larger group. We typically book home rentals through AirBnB, Booking.com or HomeAway.  Renting in the Florida Keys can be a little tricky, however, since many vacation homes rent on a monthly basis.

We were in a unique situation on our trip to Islamorada due to Hurricane Irma hitting before our stay. (Which made it difficult to find a weekly rental in good shape.) We ended up going through a rental company after the first two homes fell through due to damage. Our weekly rental home in Islamorada (located at 100 Willow Lane) 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. We really could’ve spent all day outside!

Home Rental Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

Looking for Family-Friendly Resorts in Islamorada?

Whether you’re renting a vacation home or staying at a resort property in Islamorada, I definitely recommend booking early.  If you’re looking for more of a resort setting in Islamorada, Drop Anchor Resort offers reasonably priced accommodations with good reviews. For a higher-end family friendly resort in the Florida Keys, Cheeca Lodge is a great option as well. (Full disclosure, I personally haven’t stayed at either resort, but my parents have stayed at Cheeca Lodge more than once and love it.)

House Rental Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

Things to Do in Islamorada, Florida

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.

Deep Sea Fishing in Islamorada

If you have slightly older children, deep sea fishing is one of the most popular things to do in Islamorada, Florida.  The guys in our family went offshore fishing one day and had a great time with Captain Casey out of Whale Harbor Marina.  While they didn’t catch the sailfish they initially went out for, they had a great day. The water was smooth and the wahoo, red snapper and king mackerel were plentiful. (And we ate some yummy fish that night!) You can find Captain Casey at Sea Monkey Charters. My family has fished with him since this trip and highly recommends him if you’re looking for a fishing charter in Key Largo or Islamorada.

Fishing Charter Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

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. We also spotted several manatees while we were walking along the water in the neighboring streets. If you’re searching for manatees in Islamorada, I definitely recommend going early in the day before the sun gets too hot.

Theater of the Sea

If you’re looking for a fun way to come up close to Florida’s marine life, Theater of the Sea should be on your list of things to do in Islamorada. Theater of the Sea is perfect for kids of any age, 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 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 at Theater of the Sea.

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.

Theater of the Sea is located at 84721 Overseas Hwy (Mile Marker 84.5) in 
Islamorada, FL. For more on Theater of the Sea’s hours and ticket pricing, check out the website here.

Feed the Tarpon at Robbie’s in 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.

Robbie’s of Islamorada is located at 77522 Overseas Highway (mile marker 77.5) in Islamorada, FL. For more on visiting Robbie’s Marina, check out the website here.

Pelicans Tarpon Fish Robbie's Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

Visit One of Many Parks and Beaches in Islamorada

One thing that many visitors to the Florida Keys don’t realize is that there aren’t really large, public beaches in the Keys. (If you’re looking for white sand beaches, Siesta Key and Sarasota is the place for you!) Many rental properties and resorts in Islamorada are either beachfront or have access to a private beach. If you’re someone who wants to be beachside every day, be sure to look for a property in Islamorada with access to a beach. Our home rental did not have direct beach access since it was on an inlet, but we did have access to a nearby private beach during our stay.

Anne’s Beach has long been the most popular and beautiful sandy beach in Islamorada. As of August 2019 it’s still closed for repairs from Hurricane Irma, but I have a feeling it’ll reopen by 2020. (Stay tuned!) Islamorada offers several other public parks with trails, picnic tables and play structures.

Related Post: 7+ Fun Things to do in Sarasota with Kids

Beaches in Islamorada Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

Take an Overnight or Day Trip to Key West

Key West is 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 during our week in Islamorada.

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.  During our day in Key west, we also took the requisite photo op at the Southernmost Point and spent time aimlessly walking around.

Kid-Friendly Restaurants in Islamorada

We made a lot of family meals at home during our trip, but there are so many great family friendly places to eat in Islamorada as well. 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 favorite restaurants in Islamorada with outdoor seating.

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 Restaurant Outdoor Seating Islamorada Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

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.

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.

Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

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!

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 bring your own fish restaurants Family Vacation in Islamorada Florida Keys with Kids Toddling Traveler

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 Family Vacation Florida Keys with Kids Toddling Traveler

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

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

Toddling Traveler participates in the Amazon Affiliate program and may earn a small commission for any items purchased through our links. 

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Family Vacation in Islamorada Florida Keys with Kids
Family Vacation in Islamorada Florida Keys with Kids

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