A vacationer’s guide to Islamorada, Florida


With its fantastic beaches and glorious weather, it’s not hard to see why Islamorada is one of Florida’s most visited destinations. 

Known as “The Village of Islands”, Islamorada is a collection of 5 small islands in the Florida Keys. A true taste of paradise, the area is famed for its beautiful coastline, crystal clear water, and tropical climate. 

Planning to visit? With our luxury Florida Key resort vacation homes, you can be certain of a scenic getaway to remember. Set within our exclusive Islamorada resort, couples, groups and families can easily find their perfect oceanfront rental. Accompanied by an on-resort pool, beach, bar, marina and other resort amenities, a Top Villas Florida Key’s vacation promises to be as astounding as the sunsets on the doorstep.

Our handy guide will tell you everything you need to know about Islamorada Florida!

Where is Islamorada?

Located in Monroe County, among the Florida Keys, Islamorada is made up of 5 separate islands; Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key, and Plantation Key.

Measuring only 20 miles long, this village of islands is situated exactly halfway between Miami and Key West. When traveling from Islamorada by car, it will take around 90 minutes to reach either destination.

Islamorada at sunset

The best time to visit

As Florida has some of the mildest winters in the US, December through May is peak season in Islamorada. Although temperatures are still reasonably high, the humidity is much lower and rainfall is rare. Accommodation in Islamorada around this time will get booked up fast!

With very little rainfall, spring in Islamorada is warm and humid. This is one of the busiest seasons for tourism, so vacation rentals and activities may cost slightly more.

Naturally, summer is the hottest season. Temperatures and humidity are high so afternoon thunderstorms are quite common, especially during June. As the weather is so unpredictable, you’re more likely to get a great deal on accommodation during the summer months.

September is the wettest month of the year, and by October, temperatures are considerably cooler. The islands are a lot quieter during fall, so if you’d prefer to avoid the crowds, it’s a good idea to visit Islamorada during October or November.

Although the Florida Keys aren’t usually at risk of hurricanes, they can still be affected by the Atlantic hurricane season. From June through November, the islands can be hit with storms and strong winds. If you’re travelling around this time, it’s a good idea to check the weather regularly before you go.

Where to stay in Islamorada

There are a number of hotels in Islamorada, but one of the best ways to experience the island is by staying in a private rental. 

Nestled along miles of private shoreline, our Islamorada vacation homes are available in a range of styles and sizes. From luxurious waterfront villas to stylish hotel suites, our rentals are all situated within the exclusive Islands of Islamorada Resort.

Luxury accommodation in Islamorada

The Islands Resort offers guests a personalized and intimate experience, centered around the water. Guests will have access to an array of on-site amenities, including two oceanfront swimming pools, spa services, fitness activities and a private beach.

If you want to plan an activity or experience away from the resort, the on-site concierge will arrange everything for you.

Things to do in Islamorada


Try fishing

Positioned between the Atlantic Ocean and the Gulf of Mexico, Islamorada is on the migration route for large fish. Often referred to as the ‘sports-fishing capital of the world’, the waters around the islands are packed with different species. You can expect anything from marlin and mahi-mahi – to tuna and tarpon!

The opportunities for fishing in Islamorada are endless. Private boats, group trips, and kayak fishing are all available, all year round. If you’re a beginner, it is a good idea to charter a boat with a guide. Local guides will be able to teach you the basic skills of fishing – and take you to the best spots! 

If you’d rather keep your feet on the ground, there are also plenty of inland options too! There are several miles of bridges running between the islands, most of which are closed to traffic. Not only do these offer great fishing opportunities, but the views across the water are also pretty amazing too!

Take to the water

Islamorada is famed for its abundance of watersports and activities. The open oceans and quiet beaches are perfect for an assortment of year-round fun! Whether you prefer sailing or swimming, there is something for everyone!

Kayaking and paddleboarding are fantastic and relaxing ways to explore the islands. If you’re up for something a bit more adrenaline-fuelled, you can always try parasailing, kite sailing, or windsurfing. 

With such a unique population of marine life, the crystal clear waters around Islamorada are also a paradise for divers. Perfect for both scuba diving and snorkeling, you’ll find miles of reefs, ledges and shipwrecks hidden beneath the water, all teeming with beautiful fish and colorful coral. 

There are a number of different snorkeling tours available in Islamorada, all of which guarantee visitors an unforgettable underwater adventure!

Hit the beach

With 5 different islands to explore, Islamorada is the ideal destination for a beach vacation. There are a number of different public beaches across the islands, each with its own unique charm. 

Anne’s Beach is one of the most visited beaches in Islamorada, so it does tend to get quite crowded during peak times. If you’re just looking for some relaxed sunbathing and swimming, this is the right place for you. Dogs are also allowed on the beach, so if you’re traveling with a furry friend, this is your best option. 

If you are looking for something less-touristy, the Library Beach is a bit of a hidden gem. Offering excellent views across the water, this small stretch of secluded coastline is perfect for a picnic. You can paddleboard and kayak in the protected waters here, but if you’re hoping to swim, this unpredictable water isn’t great – reef sharks are often spotted floating by! 

Although there is a small entry fee, the Long Key State Park is definitely worth a visit. The beach here offers some of the best views across the Atlantic Ocean. Although it can be a little rocky, the clear, shallow waters are great for swimming, snorkeling, and diving. Away from the beach, you will also find a number of nature trails, picnic areas, and hiking opportunities.

If you’re staying within the exclusive Islands of Islamorada resort, you’ll also be able to enjoy free entry to the resort’s private beach. The ultimate relaxation destination, this scenic stretch of paradise offers beautiful views across the water.

As a resort guest, you will have access to a number of beach activities, including snorkeling, paddleboarding, and kayaking. If you’d rather just relax in the sun, the resort’s waterfront bar is always open for beachside cocktails!

Islamorada pelican

Explore the history

First discovered by Spanish explorers in 1513, all of the islands in the Florida Keys have a rich history. Over the years, Islamorada in particular has been challenged by storms, shipwrecks, hurricanes – even pirates!

The Florida Keys History and Discovery Foundation is an oceanfront museum, packed with information, artifacts, and exhibitions about the island’s colorful past. 

If you’re keen to learn more about Islamorada’s fascinating history, the museum also hosts a popular walking tour. This ten-stop journey covers everything from the arrival of the pioneers – to the island’s history of hurricanes.

If you’d rather explore what’s going on beneath the islands, the History of Diving Museum is definitely worth a visit. Originally just a small assemblage of relics, this museum now hosts one of the world’s largest collections of diving equipment and memorabilia.

The museum is dedicated to preserving artefacts and documents related to the history of diving, and its connection to the Florida Keys. Permanent exhibitions cover everything from underwater photography to deep-sea exploration and coral reef restoration.

Meet the wildlife

If you’d like to see the Islamorada wildlife in its natural habitat, there are a number of boat tours on the island. If you prefer to get up close and personal, Robbie’s Marina is a must-visit!

Robbie’s Marina is a hub for watersports, restaurants, and shops, however, the main attraction here is the tarpon feeding. For $5, you can pick up a bucket of fish and feed the huge tarpon that reside in the area.  These enormous fish are not shy, and to see them jump out of the water to feed is an unforgettable experience! 

If you’re visiting Islamorada with kids, Theater of the Sea is another fantastic way to interact with the local wildlife. Open since 1946, this marine mammal park is home to a huge variety of aquatic animals and reptiles.

General admission will allow you access to the dolphin and sea lion shows a bottomless boat ride, and a fish and reptile tour. For an additional cost, the park also offers a number of animal interaction programs.

Booking a stay

When you book with Top Villas, not only will you get beautiful accommodation at great prices, you’ll also benefit from our amazing customer service. Whatever your preferences, our expert team will be on hand to help you find the right home.

What’s more, booking a stay couldn’t be easier.  Just follow our simple online booking process, and you can secure your dream vacation home instantly. Our website makes it easy to check availability, get a quote, and book instantly online. Alternatively, you can submit an inquiry and we’ll get straight back to you.

You can check out our full range of vacation homes in Islamorada here.