Vacation Rentals - Beach Houses, Condos, Cabins, Apartments & Vacation Homes | Tripping.com

Find Vacation Rentals in Islamorada

Islamorada
Anytime
Guests

Popular Islamorada Vacation Rentals

Find the perfect Islamorada vacation rental

House Islamorada
e.g. 9/3 - 9/10 (Sat - Sat)
$1,008 per night
House ∙ 8 guests ∙ 3 bedrooms
4.8
"Excellent" (8 ratings)
Islamorada, Monroe County, Florida, United States
Free cancellation
Details
HomeToGo
Details
Motel Islamorada
e.g. 9/18 - 9/25 (Sun - Sun)
$235 per night
Motel ∙ 14 guests ∙ 1 bedroom
3.6
"Good" (1140 ratings)
Islamorada, Monroe County, Florida, United States
Details
Traveluro
Details
Aparthotel Islamorada
e.g. 8/21 - 8/28 (Sun - Sun)
-42%
$305
$177 per night
Aparthotel ∙ 14 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
Details
Expedia
Details
Aparthotel Islamorada
e.g. 10/29 - 11/5 (Sat - Sat)
-48%
$258
$134 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
4.0
"Very good" (560 ratings)
Islamorada, Monroe County, Florida, United States
Free cancellation
Details
Expedia
Details
Condo Islamorada
e.g. 9/17 - 9/24 (Sat - Sat)
$314 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.7
"Outstanding" (18 ratings)
Islamorada, Monroe County, Florida, United States
Free cancellation
Details
FlipKey
Details
Resort Islamorada
e.g. 8/20 - 8/27 (Sat - Sat)
$419 per night
Resort ∙ 6 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
Details
HomeToGo
Details
Resort Islamorada
e.g. 8/20 - 8/27 (Sat - Sat)
$419 per night
Resort ∙ 2 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
Details
HomeToGo
Details
Resort Islamorada
e.g. 6/4 - 6/11 (Sat - Sat)
$474 per night
Resort ∙ 4 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
Details
HomeToGo
Details
Motel Islamorada
e.g. 8/20 - 8/27 (Sat - Sat)
$193 per night
Motel ∙ 4 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
Details
HomeToGo
Details
View more

Vacation rentals and apartments with air conditioning

House Aircondition Islamorada
e.g. 9/3 - 9/10 (Sat - Sat)
$1,008 per night
House ∙ 8 guests ∙ 3 bedrooms
4.8
"Excellent" (8 ratings)
Islamorada, Monroe County, Florida, United States
Free cancellation
Aircondition
Details
HomeToGo
Details
Motel Aircondition Islamorada
e.g. 9/17 - 9/24 (Sat - Sat)
$218 per night
Motel ∙ 14 guests ∙ 1 bedroom
3.6
"Good" (1140 ratings)
Islamorada, Monroe County, Florida, United States
Aircondition
Details
Traveluro
Details
Motel Aircondition Islamorada
e.g. 8/13 - 8/20 (Sat - Sat)
-68%
$567
$182 per night
Motel ∙ 14 guests ∙ 1 bedroom
3.8
"Good" (1491 ratings)
Islamorada, Monroe County, Florida, United States
Aircondition
Details
Expedia
Details
View more

Apartments and vacation rentals with a kitchen

House Kitchen Islamorada
e.g. 5/28 - 6/4 (Sat - Sat)
$469 per night
House ∙ 14 guests ∙ 2 bedrooms
4.7
"Outstanding" (24 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Expedia
Details
Aparthotel Kitchen Islamorada
e.g. 8/21 - 8/28 (Sun - Sun)
-44%
$313
$177 per night
Aparthotel ∙ 14 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Expedia
Details
Condo Kitchen Islamorada
e.g. 10/1 - 10/8 (Sat - Sat)
$262 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.2
"Very good" (188 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
Expedia
Details
View more

Vacation rentals with Wi-Fi

Aparthotel Internet Islamorada
e.g. 8/27 - 9/3 (Sat - Sat)
-48%
$258
$134 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
4.0
"Very good" (560 ratings)
Islamorada, Monroe County, Florida, United States
Free cancellation
Internet
Details
Expedia
Details
Condo Internet Islamorada
e.g. 10/29 - 11/5 (Sat - Sat)
$314 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.7
"Outstanding" (18 ratings)
Islamorada, Monroe County, Florida, United States
Free cancellation
Internet
Details
FlipKey
Details
Condo Internet Islamorada
e.g. 10/1 - 10/8 (Sat - Sat)
$262 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
Internet
Details
HomeToGo
Details
View more

Frequently Asked Questions

What is the price of vacation rentals in Islamorada?

Usually, a stay in Islamorada starts at $134 per night.

Can I book a vacation rental in Islamorada?

You can find 947 available vacation rentals in Islamorada.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Islamorada Information

About Islamorada

Islamorada, Florida is a beach town located in the Florida Keys south of the Florida mainland. It’s known as the “Sport Fishing Capital of the World” and is also very popular for scuba diving, snorkeling, and other ocean activities. Come for the beach and stay for the friendly locals and relaxing atmosphere.

Things to do in Islamorada

Islamorada is a very popular spot in the Florida Keys and you’ll never be bored. It is known as the “Sport Fishing Capital of the World” for a reason - the fishing here is excellent. If you want to go fishing, but don’t have your own boat, check out fishing charter companies in the area, such as A Pirates Choice Deep Sea Fishing Charters. There are also charters available at Robbie’s Marina, where you can purchase buckets of bait to feed the tarpon off the marina dock. You can also rent kayaking, snorkeling and scuba gear there. Scuba diving has become huge in Islamorada with wide variety of shallow coral reefs, mini walls and shipwrecks. Some of the best diving areas include The Eagle Shipwreck, Davis Reef, Alligator Reef and Crocker Wall, among others. When in Islamorada, check out the 11-acre Indian Key Historic State Park and view the remains of a shipwreck salvage community from the 1830s. There are also several hundred yards of well-maintained trails that line the interior of the island. Experience one of the world’s largest collections of historic dive equipment and trace 3,000 years of diving at the Florida Keys History of Diving Museum. Another one of Islamorada’s top attractions is Theater of the Sea, the second oldest marine mammal facility in the world, where you can view dolphin and sea lion shows and even get in the water and swim with them. For beer lovers, there are two great island breweries in Islamorada to check out: head to Florida Keys Brewing Company and the Islamorada Beer Company Brewery to sample the beers and enjoy the friendly environment. There are many small beaches to check out in Islamorada including Anne’s Beach, Sea Oats Beach and Kite Beach, which are all great for relaxing and taking in the beautiful sunsets.

Day trips from Islamorada

There are some great day trips you can take from Islamorada despite its location in the secluded Florida Keys. For a quick trip, just a 15-minute drive from Islamorada is Key Largo, one of the most popular areas in the Florida Keys. You can easily spend a day in Key Largo, which is one of the most popular scuba diving cities in the world. There are many fun classes and instruction courses to take in Key Largo and the sites that you’ll dive in mostly fall in the 25-40-foot depth range in warm water that doesn’t have currents that could bother you. The Molasses Reef is a great place to dive in Key Largo, where you’ll see great wildlife with different types of fish and maybe even turtles in the sandy area. Enjoy a unique experience swimming with dolphins at Dolphins Plus, and check out more great boat and fishing tours out on the water. You can also get out of the keys and take a 1.5-hour drive north to Miami, Florida, one of the most popular tourist destinations in the country. Once you’re there, you can experience great beaches in Miami as well as the cultural vibrance of Florida with salsa dancing, delicious restaurants throughout the city, and art like the famous Wynwood Walls. You can also visit Zoo Miami or you can catch a concert or Miami Heat basketball game at the American Airlines Arena.

Islamorada Accommodations

There are great vacation rentals throughout the Florida Keys, and Islamorada is no exception. You can’t really go wrong on choosing where to stay, considering that mostly everything is on the water. The Overseas Highway is what runs through the keys and anything off of that will put you in a good spot for your vacation in Islamorada.

Transportation in Islamorada

You’ll definitely need a car in order to get around whether you drive down from the Florida mainland or you rent one at the airport. There is also Islamorada Taxi to help get you around if you don’t feel like driving. Consider renting a bike and riding it around the flat, scenic beach areas!

Popular Day Trips Near Islamorada

image-tag