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Islamorada Condos & Vacation Rentals

Our Favorite Vacation Rentals in Islamorada

Islamorada Vacation Rentals with a Pool

Islamorada Vacation Rentals with Wi-Fi

Islamorada Pet-Friendly Vacation Rentals

Islamorada Travel Guide

Known for its beautiful beaches, vibrant coral reefs, and colorful marine life, Islamorada is a pleasant coastal village that encompasses six of the Florida keys. It has plenty to offer visitors to Florida.

Things to Do in Islamorada

As a coastal village, of course one of the best things to do in Islamorada is to relax on one of the numerous beaches in the area. Anne’s Beach is a picturesque spot perfect for relaxation and popular for kitesurfers. Nearby, the Theater of the Sea allows visitors to witness and interact with marine life, including dolphins and manatees.

Best Time to Visit Islamorada

The spring months of March to May are the best time to visit Islamorada in order to experience hot weather without the humidity of the summer.

A Local's Guide to Islamorada Vacation Rentals

Islamorada is truly paradise. More commonly known as Islamorada village, the group of islands in the sunny Florida Keys that are known as the sport fishing capital of the world. The tranquil Islamorada Village is comprised of a group of tropical islands spanning eighteen miles off the southern tip of Florida.

Vacation Homes

Travelers renting a vacation home in Islamorada, FL can enjoy the community’s tennis courts and will feel the warm welcome of the islands up-scale small town atmosphere. While in Islamorada, vacationers can rent a boat or hire a guide for a one of a kind, world class fishing, diving, or snorkeling experience.

See & Do

A perfect day in Islamorada begins with coffee in your vacation rental, while enjoying a stunning ocean view. Then head to the beach to relax, head out to fish, or explore Windley Key Fossil Reef Geological State Park, where visitors will learn the history of the region and explore unique fossilized coral reefs. Experience marine life first-hand at Islamorada’s Theater of the Sea, where guests can swim with Sea Lions. End the day with the Islamorada. treasured seafood.


Superb Seafood is the hallmark of the Islamorada food scene. Enjoy your own fresh catch, or head to one of the excellent eateries to enjoy all the islands have to offer.

Condos in Islamorada

The colorful city of Islamorada, known as the sport-fishing capital of the world, is surrounded by beautiful beaches, encompassing six of the Florida Keys, including the beautiful Plantation Key and Windley Key. Although the biggest draws to the area are the stunning coast, condo rentals, and many coral reefs, people also come looking for an Islamorada condo rental due to the many things to do and see in the area.

Windley Key Fossil Reef Geological State Park offers plenty of outside adventure, and the History of Diving Museum gives a good insight into the world below the waves. If that’s not enough, Bud N’ Mary’s is a world-famous fishing marina, while visitors can even swim with dolphins at the Theatre of the Sea.

Vacation homes in town are especially impressive, partly because the majority come with stunning panoramic views of the ocean and beyond. Oceanfront vacation rentals are plentiful, and many come with a swimming pool, full kitchens, and a washer dryer. No matter your party size, there will be rentals in Islamorada perfect for your needs, be it a 1 bedroom 1 bathroom home, or something much bigger. Waterfront homes with ocean views are also not uncommon in the Florida Bay area.

Price and Availability in Islamorada

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The most expensive month to stay in a vacation rental in Islamorada is in July, while the cheapest month is in February. The most popular time to book a vacation rental in Islamorada is in the high season in February. Islamorada has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Islamorada tends to be Friday, while the most expensive day tends to be Sunday. Vacation homes in Islamorada tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.

The Weather in Islamorada

97º 74º
92º 74º
93º 74º
91º 70º
88º 56º
88º 56º
82º 49º
85º 65º
88º 57º
91º 67º
89º 73º
95º 73º
Rainy days
This climate histogram shows you the weather patterns in Islamorada. The warmest months in Islamorada are June and July, when temperatures reach 97 ˚F. The coolest month is January, when temperatures drop to 49 ˚F. The wettest month in Islamorada is May with 9.7 inches of rain, while the driest month is February with 0.05 inches of rain.

What Expert Travelers Think

Vacation Rentals in Islamorada

At we have rentals from all of your favorite providers - Airbnb, RedAwning, Priceline and more. We have 1,276 vacation rentals, hotels and other accommodation types in Islamorada ranging from budget options to extravagant places to stay. On average, an accommodation in Islamorada will cost you $751 per night.

Those needing to get some work finished during their trip to Islamorada can choose from 452 places to stay that have WiFi. We have 18 accommodations that include a breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 45 accommodations that have gym facilities. If you're planning on getting to Islamorada by car, be sure to choose from 459 accommodations that provide parking. 158 places to stay come with a pool or jacuzzi

AllTheRooms has 121 pet-friendly places to stay in Islamorada, so if you're traveling with your cat or dog you won't have any trouble.

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from many providers in Islamorada, including 239 places to stay from Airbnb, 9 accommodations from RedAwning and 6 places to stay from Priceline

538 of our accommodations in Islamorada have been reviewed and rated. 39% are rated excellent or good. 247 places to stay in are instantly bookable.

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