Find Vacation Rentals in Islamorada

Highlights Islamorada

  • Island rentals
  • Destination in Florida
  • Family getaway
  • Outdoor adventures
  • Nature getaway
  • Hiking trails

Best Vacation Rentals in Islamorada

Guests agree: these stays are highly rated for location, cleanliness, and more.
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Upper Matecumbe Key, Islamorada
Vacation Rental • 743 ft² • 1 Bedroom
5.0
(20 reviews)
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air conditioned and there are ceiling fans throughout. The kitchen is modern and equipped with all the necessary appliances. The property is a nature lovers dream with resident fish, lobster, an octopus and an occasional manatee in the marina, iguanas that sun themselves by the boat basin and pe...
from $243 / night
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Islamorada, Monroe County
Vacation Rental • 1195 ft² • 2 Bedrooms
4.7
(20 reviews)
License # VR-282 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th floor. Tile floors, modern kitchen with stainless steel appliances and granite counter tops. 3 large flat screen TV's for your viewing pleasure. Large balcony partly screened. The guest bath has a soaking tub and the master bath a beautiful tiled walk in shower. The guest bedroom has a king sized 4 poster bed, with spectacular views of the ocean through sliding doors which open onto the balcony. The master bedroom has a 4 poster king sized bed with a view of the ocean throu...
from $312 / night
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Upper Matecumbe Key, Islamorada
Vacation Rental • 5253 ft² • 5 Bedrooms
5.0
(20 reviews)
OSPREY BAY VILLA! Wonderful Bay front Home in the heart of Islamorada in the fabulous Florida Keys for rent by the week, or month; offering Incredible Panoramic Bay and Sunset Views. Heated pool & hot tub, sunning decks galore. Deep water dock & boat basin. Elegant, yet casual, spacious living room with coral rock fireplace, wet bar, open dining room, atrium garden,& gourmet kitchen. Sleeps 10-12 people comfortably. Private south wing offers 3 bedrooms; 1 with1 king bed, 1 with 1 queen bed, another 1 with 2 queen beds, and 1 full bathroom with bathtub & separate shower, doub...
from $1,143 / night

Prices and availability

Vacation rental prices Islamorada

$499for 3 Dec - 10 Dec
$594 annual average
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Average price per week

Vacation rentals availability Islamorada

21%for 3 Dec - 10 Dec
17% annual average
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Percentage of available rentals

Vacation rentals in Islamorada

Stunning rental locations in Islamorada

Plan your next vacation on the beautiful island of Islamorada. The destination of Islamorada encompasses five of the Florida Keys and it is located in the Monroe County of the state of Florida, United States of America. Situated right in between Miami and Key West, the area includes Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key. The area of Islamorada is known for its stunning coral reef, the gorgeous tropical landscape and the countless water sports that you can enjoy during your visit. The name of this area comes from the early Spanish explorers and it translates to "purple island" in Spanish.

Vacation Rentals in Islamorada

You can find countless stunning vacation rentals while visiting Islamorada. Whether you wish to be located closer to the buzzing center, immersed in nature or have your accommodation beachside, this destination will be able to provide it with all. Imagine waking up in the morning to the sound of the waves crashing on the beach right outside your window. Take a stroll around town to check out the boutiques and cafes located just a stone throw away from your house. Spend an afternoon swimming in your private pool or having a barbecue with your friends in your garden. These are just some of the memories you could be making with accommodation in Islamorada.

Vacations in Islamorada

The area and getting around

How to get to Islamorada

There are various ways to make your trip to Islamorada with different modes of transportation. Being located between Key West and Miami, you will be assured that the journey will be easy to make from wherever you are coming from. If you're driving from Miami or anywhere north of Islamorada, you will have to arrive at the end of the Turnpike at US 1 in Florida City and head south on the road to reach your destination. This same road is taken by regional buses and private buses to connect Islamorada with nearby major cities. If you choose to fly to your destination, the closest airport with commercial flights to national and international destinations will be the Miami International Airport.

Where to eat in Islamorada

Being located right in the sea, you will find that there will be plenty of delicious restaurants providing fresh seafood. However, Islamorada has plenty of other options to choose from regarding cuisine and styles. One of the local favorites is the Hungry Tarpon Restaurant. This eatery will provide you with a true conch atmosphere and Caribbean-inspired cuisine. The restaurant is situated inside an old marina and fish shack and you will be able to choose to dine indoors or on their deck. Another great place to have some food is Ciao Hound. This Italian restaurant has a menu filled with Tuscan flavors and it uses only fresh ingredients which are locally sourced.

Travelers and activities

Islamorada for outdoor explorers

There are numerous ways you can enjoy discovering the stunning tropical landscape of Islamorada. Go ahead and spend a day at Anne’s Beach. This beach was named after a famous environmentalist that dedicated her life to preserving South Florida’s natural habitat. Here you will be able to stroll on a boardwalk that takes you through mangroves, tidal marshes, and wetlands. Another fantastic place to learn about the local flora and fauna is the Indian Key Historic State Park. This ten acres park is only reachable by boat and it is a popular spot for hikers that want to visit the abandoned early 19th-century fishermen town.

Islamorada for family activities

If you plan to make your vacation to Islamorada with your family, try out these activities altogether for a delightful time. One of the best activities to do with the whole family is to visit the Theater of the Sea. This place will allow you to admire dolphins, learn about them, as well as swim with them. Another great place to visit all together is the Alligator Reef LightHouse. This in-sea lighthouse can only be reached with a chartered boat or with a rental boat and you will get the chance to snorkel around the crystal blue waters and admire the world-famous coral reef of the Keys.

Did you know that Islamorada was incorporated only on November 4, 1997?

Top 5 travel tips for Islamorada

1. History of Diving Museum

Learn about the history of diving. This museum has been open and collecting items used for sea exploration for over decades. You will be able to find displays that include diving equipment, photographs, and first-hand historical accounts of sea adventures.

2. Whale Harbor Restaurant and Seafood Buffet

Dine with some exquisite and fresh seafood. This restaurant provides you with everything starting from shrimp and lobster to oysters and fresh local fish on their rooftop bar.

3. Keys History and Discovery Center

Discover the local history. This establishment aims to preserve the unique history of the Keys while providing you with exhibits and displays in their waterfront building.

4. Blond Giraffe Key Lime Pie Factory

Have a taste of the globally famous Key Lime Pie. This restaurant provides the state’s best key lime pie in a very casual and friendly atmosphere.

5. Windley Key Fossil Reef Geological State Park

Explore the fossils of the area. In this stunning park, you can walk through trails and admire the vast fossil deposits, many of which can be dated to 100,000 years ago.

FAQs: Vacation Rentals in Islamorada

How much does it cost to book a vacation rental in Islamorada?

With an average cost of $478 per night, Islamorada lies at the upper end of the price range for vacation rentals in the USA.

When are vacation rentals cheaper in Islamorada?

Those who want to save as much as possible travel to Islamorada in October, August, or September, the cheapest months of the year, with average prices of $397, $437, and $454 per night, respectively, based on the previous year.

When does the price of vacation rentals in Islamorada go up the most?

When booking a vacation rental in Islamorada, the highest prices are usually seen in the month of February (with an average of $614 per night), followed by March ($531), and then April ($501).

Should I plan a trip to Islamorada well in advance?

It is better to book sooner than later in Islamorada as only 11% of the properties remain available throughout the year, according to last year's data.

What are the best months for a spontaneous getaway?

The best months to find available accommodation in Islamorada are August (the average amount of properties that are free reached 28% of the total last year), September (21%), and October (20%).

How many vacation rentals are there in Islamorada?

We have 70 rentals for you in Islamorada, provided by our 3 local and international partners.

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