Florida Keys with Kids: Islamorada Family Vacation

My parents visit Islamorada (village of islands) in the Florida Keys almost every year in the late winter.  With a new baby in tow, 2018 was the perfect year for a relaxing Florida Keys family vacation.  And we couldn’t have been more excited to escape the cold for a family vacation in Islamorada in the Florida Keys. The warm weather, clear blue water, and laid back vibe makes Islamorada the perfect spot to visit the Florida Keys with kids (or without!) 

If you’re visiting Islamorada with a baby or toddler 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

Disclaimer: Toddling Traveler participates in Amazon Affiliates and other affiliate programs. That means we may earn a commission for qualifying purchases through our links, at no charge to you.

Table of Contents: Florida Keys with Kids

How to Get to Islamorada, Florida

There isn’t a major Florida Keys airport in the northern part of the Florida Keys. That said, the best airport to fly into to get to Islamorada is either Fort Lauderdale or Miami International Airport.  (Both are most cost effective and take less time than flying into the Key West airport.) We flew into Fort Lauderdale-Hollywood International Airport since Southwest Airlines flies nonstop there. I also find it much easier to navigate Ft Lauderdale’s airport than Miami. We rented a car and drove about 2 hours south to get to Islamorada, which is just past Key Largo.

Related Post: Flying with a Baby: Tips for Before, During & After Your Flight

The overseas highway (aka the Florida Keys highway) is very scenic and includes mile markers along way. The mile markers in the Keys are an easy way to designate both location and distance. Islamorada is generally located from mile market 91 to mile marker 73. If you’re looking to do a Florida Keys road trip, it’s a beautiful drive regardless of where you’re starting and ending.

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

Best Time of Year to Visit Florida Keys

Planning a Florida Keys family vacation and not sure when to go? Weather-wise, the best time to visit Florida Keys is typically in November, December, March or April when the weather isn’t super hot or rainy. Unfortunately, with the holidays and Spring Break, those months also tend to be the most expensive times to visit the Florida Keys.

My family prefers to visit the Florida Keys in February. The weather in the Florida Keys in February is typically warmer (high 70s/ low 80s F) by the end of the month. The prices are less expensive prior to Florida being inundated with spring breakers. On our recent Islamorada vacation, the weather in Islamorada in February was in the high 70s F, with cooler mornings and warmer afternoons. (Florida Keys house rentals or resorts with a heated pool are definitely recommended for this reason.)

Islamorada, FL Vacation Rentals

If you’re visiting the Florida Keys for family vacation, I definitely recommend getting a rental home if you’re traveling with a larger group. We typically book home rentals through AirBnB, VRBO and Booking.com.  There are a few differences between AirBnB and VRBO, but both have a great selection of options for house rentals in Islamorada. Keep in mind that house rentals in the Florida Keys can be a little tricky to find, since many vacation homes rent on a monthly basis.

For Islamorada, Florida AirBnB rentals, search here.

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 Islamorada, Florida VRBO rentals fell through due to damage. We ended up with a great 5-bedroom home in Lower Matecumbe Key, but unfortunately it’s no longer listed.

This home is in the same area of Islamorada with access to the community beach that our property had. Although it’s smaller, it has the in-ground pool, covered patio and water access that we loved.

Search Islamorada, Florida AirBnBs here.

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.)

For more Islamorada, Florida resorts and hotels, search here.

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

Things 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 the Florida Keys with kids or without, there are so many fun things to do in Islamorada and the rest of 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.

Islamorada Fishing Charters

Deep sea fishing in Islamorada, FL is one of the most popular things to do in Islamorada, FL.  The guys in our family went offshore fishing one day and had a great time with Captain Casey, one of the best Islamorada fishing guides.  While they didn’t catch the sailfish they initially went out for that day, 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, located at the Baker’s Cay Resort marina. My family fished with him a few times and highly recommends him if you’re looking for an Islamorada or Key Largo fishing charter.

Looking for Florida Keys boat rentals to go fishing on your own instead? You can find Islamorada, Florida boat rentals here.

Islamorada Fishing Charter Florida Keys with Kids Toddling Traveler

Walk with the Manatees in Florida Keys

Wondering where to find Manatees in Florida in their natural element? 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. (Their proximity to the homes and docks make Islamorada a great place for kayaking with manatees in Florida too.)

We also spotted several manatees while we were walking along the water in the neighboring streets. If you’re searching for manatees in the Florida Keys and specifically Islamorada, I 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 Florida Keys with kids. 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 these Florida Keys aquarium encounters 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 at Robbie’s, with several local vendors for handmade souvenirs and paintings.

Robbie’s is also one of the best places for a Florida Keys kayak rental or an Islamorada jet ski rental, given the access to calm waters and sea life. In addition to the variety of water sports and activities, there’s a restaurant onsite at Robbie’s. It’s the perfect spot if you’re searching for Islamorada restaurants on the water with life music.

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 the Islamorada, Florida Beaches & Parks

One thing that many visitors to the Keys don’t realize is that there aren’t a ton of large, public Florida Key Beaches. (If you’re looking for white sand beaches, Siesta Key in 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 rental in Islamorada with beach access.

Anne’s Beach has long been the most popular and beautiful sandy beach in Islamorada. If you’re wondering, has Anne’s Beach reopened from Hurricane Irma, the answer is yes! After a couple years of repairs, Anne’s Beach is now open. It offers a few hundred feet of boardwalk, restrooms and other faculties. We only saw it from a distance since it was closed during our trip. My parents always loved going to Anne’s Beach though, and it’s supposed to be a very calm beach if you’re visiting Islamorada with kids.

Islamorada also offers several other public parks with trails, picnic tables and play structures.

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

Spend One Day in 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 during our Islamorada vacation. That gave us 24 hours in Key West for a kid-free dinner and night out.

We stayed at the La Concha Hotel & Spa, a boutique hotel right in the heart of Key West.  The rooms are beautifully decorated and the pool and central location are perfect for any length Key West itinerary.  For dinner that night we were craving sushi and had a yummy dinner at Mangoes Key West. We also went to a few Key West bars before ending the night with an amazingly huge and yummy cookie sundae at Mattheessens Key West.  

The grandparents drove the kiddos down the next day and we visited the Key West Butterfly & Nature Conservatory.   (Definitely something I recommend if you’re looking for things to do in Key West with kids.) The look on my son’s face when seeing butterflies come right up to him for the first time was priceless. While the conservatory is small, it’s jam-packed with beautiful plants, birds and butterflies.  

Another “can’t miss” thing to do in Key West is a photo op at the Southernmost Point. Be sure to also leave some time for walking around and taking in the sites, since Key West is such a unique little town.

For Key West excursions and more fun things to do in Key West, search here.

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

Known as one of the best restaurants in Islamorada, Lazy Dayz was a great choice for our first night out.  The restaurant has a huge menu with a ton of fresh options for seafood in Islamorada. The restaurant has ample space with a number of indoor/ outdoor seating areas. Lazy Dayz is also one of few Islamorada restaurants on the beach, and it’s a great place to catch live music right.

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, we still had a great meal and I definitely recommend it if you’re looking for breakfast in Islamorada. The service is quick and the kids loved all the birds and fish by the water.

Bayside Gourmet is another place that’s known for having the best breakfast in Islamorada. It was closed on the day we were out for breakfast, but it’s on our list for the next trip!

Morada Bay Beach Cafe

If you’re looking for a more upscale cafe in Islamorada, Morada Bay Beach Cafe is a great lunch spot right on the beach. My Beach Cafe Salad with ahi tuna was super fresh, and I recommend 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 in Islamorada, which is an attraction in itself.

Have you been to Islamorada or the Florida Keys? Please share in the comments if you have any favorite places to eat or fun things to do in the Florida Keys!

Related Posts:


Like this Post? Click to Pin for Later:

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


10 thoughts on “Florida Keys with Kids: Islamorada Family Vacation

  1. Great post! Thank you so much for all the info. I am considering planning a family road trip from Miami to the Keys

  2. We drove through Islamorada on our way to Key West, we stopped for lunch but I really wish we had more time there. This post has really got me wanting to return!

Leave a Reply