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Islamorada Condos & Vacation Rentals

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  4. Islamorada

Our Favorite Vacation Rentals in Islamorada

  • Islander Bayside Townhomes and BoatSlips
     3-star Country House
    Booking.com
    From
    $606
  • Family Paradise Florida Keys Beautiful Islamorada
     2br Home/Apartment
    Airbnb
    From
    $260
  • "Lucky Find" Troller in paradise-Amazing Vacation
     2br Home/Apartment
    Airbnb
    From
    $466
  • Island Sanctuary Islamorada
    Excellent2br Home/Apartment
    Airbnb
    From
    $254
  • 2BR ~ Tropically Inspired Oasis
    Good2br Home/Apartment
    Airbnb
    From
    $367
  • Lets Go Glamping in Vintage Airstream
     Home/Apartment
    Airbnb
    From
    $105
  • 1BR~ Paradise Oasis
    GoodHome/Apartment
    Airbnb
    From
    $283
  • 2BR ~ Full Condo with Ocean View
    Good2br Home/Apartment
    Airbnb
    From
    $367
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Islamorada Vacation Rentals with a Pool

  • 1BR ~ Piña Coladas ~ Pool Dayz
    GoodHome/Apartment
    Airbnb
    From
    $283
  • 1BR ~ Paradise Awaits
    GoodHome/Apartment
    Airbnb
    From
    $283
  • 2BR ~ Sunrise ~ Sunsets
    Nice2br Home/Apartment
    Airbnb
    From
    $367
  • 3x ~ 2BR Breathtaking Views- Sleeps up to 18
    Good6br Home/Apartment
    Airbnb
    From
    $961
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Islamorada Vacation Rentals with Wi-Fi

  • 2BR ~ Flip Flops and Sunscreen
    Good2br Home/Apartment
    Airbnb
    From
    $367
  • 2BR ~ Paradise Awaits
    Nice2br Home/Apartment
    Airbnb
    From
    $367
  • 2BR ~ Islamorada Vacation
    Good2br Home/Apartment
    Airbnb
    From
    $367
  • 2BR ~Unwind in the Florida Keys
    Good2br Home/Apartment
    Airbnb
    From
    $367
Show all

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.

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Price and Availability in Islamorada

Most expensive
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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.
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The Weather in Islamorada

Rainy days
87° 53°
2
89° 64°
3
90° 61°
1
94° 70°
1
96° 74°
2
98° 74°
4
94° 74°
5
94° 75°
4
93° 76°
3
91° 74°
4
89° 63°
0
86° 59°
5
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Islamorada. The hottest month in Islamorada is July, when temperatures peak at 98 ˚F. The coolest month is December, when temperatures drop to 53 ˚F. The wettest month in Islamorada is June with 4.93 inches of rain, while the driest month is February with 0.3 inches of rain.

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What Expert Travelers Think

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    Amanda Alston
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  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
    Travel Better Guide

Vacation Rentals in Islamorada

Browse places to stay from all your favorite providers including Airbnb, Priceline, TUIVillas and many more at AllTheRooms.com. We have 1,406 vacation rentals, hotels and other accommodation types in Islamorada ranging from low-cost options to luxury places to stay. A typical rental in Islamorada costs on average $709 per night.

Those looking to get some work done during their trip to Islamorada can choose from 299 places to stay that have WiFi. 27 of our accommodations include a breakfast in the price. You can keep up with your workout routine by staying at one of 28 accommodations that provide gym facilities. Driving to Islamorada? Then choose one of the 301 places to stay that comes with a parking spot included. 185 accommodations have a a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 99 pet-friendly accommodations available.

572 accommodations in Islamorada have been reviewed; 40% are rated excellent or good. You can instantly book any of 337 places to stay right now.

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