Islamorada Condos & Vacation Rentals

Our Favorite Vacation Rentals in Islamorada

  • Islander Bayside Townhomes and BoatSlips
     3-star Country House
    Booking.com
    From
    $533
  • 2 bedroom yacht in the water at Islamorada
    Good2br Boat
    Airbnb
    From
    $270
  • FAMILY PARADISE FLORIDA KEYS BEAUTIFUL ISLAMORADA
     3br Home/Apartment
    Airbnb
    From
    $141
  • 57ft DeFever in Islamorada Marina
     3br Home/Apartment
    Airbnb
    From
    $509
  • Island Sanctuary Islamorada
    Excellent2br Home/Apartment
    Airbnb
    From
    $254
  • 2BR ~ Sunsets in Paradise
    Good2br Home/Apartment
    Airbnb
    From
    $401
  • NEW Secret Keys Waterfront Hideout has EVERYTHING!
    ExcellentHome/Apartment
    Airbnb
    From
    $505
  • Reserve NOW! Winter Tavernier Sleps 1-4/2-30nites
    GoodHome/Apartment
    Airbnb
    From
    $226

Check prices for these upcoming dates

Islamorada Vacation Rentals with a Pool

  • 2BR ~ Tropical Paradise ~
    Good2br Home/Apartment
    Airbnb
    From
    $401
  • 2BR ~ Tropically Inspired Oasis
    Good2br Home/Apartment
    Airbnb
    From
    $401
  • 2BR ~ Sandy Beach ~ Pool ~ Restaurant
    Good2br Home/Apartment
    Airbnb
    From
    $327
  • 2BR ~ Sunsets & Ocean Views
    Good2br Home/Apartment
    Airbnb
    From
    $401

Islamorada Vacation Rentals with Wi-Fi

  • 1BR ~ Relax ~ Ocean Views ~ Sunrise
    GoodHome/Apartment
    Airbnb
    From
    $367
  • 1BR~ Paradise Oasis
    GoodHome/Apartment
    Airbnb
    From
    $310
  • 1BR ~ Sandy Beach ~ Sunny Dayz
    GoodHome/Apartment
    Airbnb
    From
    $310
  • 2BR ~ Florida Keys Getaway
    Good2br Home/Apartment
    Airbnb
    From
    $321

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.

Food

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

Most expensive
Most availability
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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
88° 56°
1
88° 56°
1
82° 49°
0
85° 65°
0
88° 57°
1
91° 67°
4
89° 73°
10
95° 73°
1
97° 74°
5
92° 74°
4
93° 74°
1
91° 70°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Islamorada. The hottest month in Islamorada is June, when temperatures peak at 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

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

Vacation Rentals in Islamorada

Find the perfect accommodation for your trip at AllTheRooms.com. We compare Airbnb, RedAwning, Priceline and more. We have 1,611 vacation rentals, hotels and other places to stay in Islamorada ranging from cheap options to extravagant places to stay. A typical vacation rental in Islamorada costs on average $704 a night.

If you would like to stay connected during your vacation, then you can choose from over 317 accommodations in Islamorada that have WiFi. 28 of our accommodations come with breakfast in the price. You can maintain your workout routine by staying at one of 29 accommodations that provide gym facilities. Driving to Islamorada? Then choose one of the 332 places to stay that comes with a parking spot included. We track 187 vacation rentals that have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to select one of the 107 pet-friendly accommodations available.

In Islamorada AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 4 providers, including 304 places to stay from Airbnb, 6 accommodations from RedAwning and 6 places to stay from Priceline.

584 accommodations in Islamorada have been reviewed; 39% are rated highly. 334 accommodations allow instant booking.

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