Islamorada Condos & Vacation Rentals

See all 1475 deals in Islamorada

Our Favorite Vacation Rentals in Islamorada

  • Islander Bayside Townhomes and BoatSlips
    ExcellentCountry House
  • Ocean-Front Caribbean Home.
    Excellent3br Home/Apartment
  • Mangroves
  • holiday home for max. 6 persons in Islamorada, Florida
    OkayCountry House
  • Capt. Craig's Guest Quarters
  • Comfortable Clean HouseBoat in an amazing location
  • Mangroves
  • holiday home for max. 6 persons in Islamorada, Florida
    OkayCountry House

Check prices for these upcoming dates

Islamorada Vacation Rentals with a Pool

  • Mangroves
     2br Home/Apartment
  • Mangroves
     2br Home/Apartment
  • Caloosa Cove Resort & Marina (STUDIO)
  • 2BR/2BA Tropically Inspired Oasis
    Good2br Home/Apartment

Islamorada Vacation Rentals with Wi-Fi

  • 2 bedroom yacht in the water at Islamorada
    Good2br Boat
  • Hurricane Safe!Traveling Trailer
  • Comfortable Clean updated Houseboat in Paradise

Islamorada Pet-Friendly Vacation Rentals

  • Capt Craigs Guest Quarters Remodeled 1/1 Apartment
  • 57ft DeFever in Islamorada Marina
     3br Home/Apartment
  • Boat Slip w/ 1 bathroom shower
  • A Comfortable piece of Paradise with Dock slip
    Nice2br Home/Apartment

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 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 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 Weather in Islamorada

Rainy days
93 º74
91 º70
88 º56
88 º56
82 º49
85 º65
88 º57
91 º67
89 º73
95 º73
97 º74
92 º74
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 December, when temperatures drop to 49 ˚F. The wettest month in Islamorada is August with 9.7 inches of rain, while the driest month is November with 0.05 inches of rain.

What Expert Travelers Think

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  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!


Vacation Rentals in Islamorada

At we have vacation rentals from all of the leading providers - Airbnb, RedAwning, Priceline and many more. Islamorada has 1,438 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. An average vacation rental in Islamorada costs on average $731 per night.

Those needing to get some work done during their trip to Islamorada can pick from 496 places to stay that provide WiFi. 23 of our accommodations include a breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 49 accommodations that have gym facilities. Driving to Islamorada? Then choose one of the 504 places to stay that comes with a parking spot included. 171 hotels and vacation rentals have a a pool or jacuzzi

AllTheRooms has 133 pet-friendly places to stay in Islamorada, so if you're traveling with your cat or dog you won't have any problems.

AllTheRooms aggregates vacation rentals, hotels and other bespoke accommodation types from many providers in Islamorada, including 275 places to stay from Airbnb, 9 accommodations from RedAwning and 6 places to stay from Priceline

588 of our places to stay in Islamorada have been rated by previous guests. They rated 40% as excellent or good. You can instantly book any of 304 places to stay right now.

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