Islamorada vacation rentals

We found 2,120 vacation rentals — enter your dates for availability

Select from 591 houses, 90 apartments, and other vacation rentals to find the perfect place for your stay in Islamorada. Vacation homes offer the amenities you expect for your stay with friends, family, or just your pet, including parking and a garden. At the end of the day, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Travel to tranquil Islamorada

Enjoy the area's entertainment, opera and theater scene and make a vacation rental your home during your stay in Islamorada. This relaxing city is known for its fishing, seaside and diving. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Islamorada

Are you hoping to find attractions to visit during your stay? Travelers enjoy fun activities like fishing and diving. Venture out of your cozy vacation rental and experience everything that makes Islamorada a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • MarineLab Undersea Laboratory (20.3 mi / 32.7 km)
  • Jacob's Aquatic Center (16.6 mi / 26.7 km)

Exploring the natural landscape of Islamorada

Travelers appreciate the beautiful ocean views and breathtaking sunsets, which is just a taste of what Islamorada has to offer. Whether you're an active traveler or just want to take in the scenery, Islamorada is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Founders Park (4.6 mi / 7.4 km)
  • Anne's Beach (8.8 mi / 14.1 km)
  • Fiesta Key (11.8 mi / 19 km)
  • Curry Hammock State Park (25.6 mi / 41.3 km)
  • Coco Plum Beach (26.9 mi / 43.4 km)
  • Windley Key Fossil Reef Geological State Park (2.4 mi / 3.8 km)

Transportation to and around Islamorada

The nearest airport is in Marathon, FL (MTH-Florida Keys Marathon), located 30 mi (48.2 km) from the city center.

Frequently asked questions

What is the best area to stay in Islamorada when booking a vacation rental?
If you’re planning a break in Islamorada, Venetian Shores is one of the most sought-after destinations to stay. No matter your style of travel, Vrbo is sure to have a vacation rental here that’s just right for you.
What is the most popular type of vacation rental accommodation in Islamorada?
Houses are the most popular style of vacation rental in Islamorada, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect fit.
How much does it cost to rent a vacation rental in Islamorada?
Season, property type and length of stay are some things that can influence the price of a vacation home. Simply add your dates of travel to find your ideal escape. From homey country cottages to expansive villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Islamorada?
When you travel and the style and size of the property will influence the cost of your beachside stay. Enter your Islamorada travel dates to see your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to choose the features and amenities you need.
Are there pet-friendly vacation rentals in Islamorada?
Pack a travel bag and a bone for the pup in your life because Islamorada has 166 stays that throw out the welcome mat to doggie guests. Let your furriest pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Islamorada?
Mark the “pool” box in our filter tool and you can choose from 122 houses with private pools in Islamorada on Vrbo. Morning dip, sunset soak or midnight swim? How you spend your free time is up to you when your vacation property has its own swimming pool.
What are popular rental amenities in Islamorada?
Some of the most popular rental amenities people look for in Islamorada are a barbecue grill, a chef and a sauna. Whether you’re on a trip with family, pals or even pets, Vrbo vacation rentals have the best amenities for chilling out with the people you cherish the most.
Are there large group vacation rentals in Islamorada?
You can pick from 18 vacation properties in Islamorada that can host a group of 10 or more guests. Whether you’re organizing time away with the family or an event like an anniversary, there’s plenty of space to get your loved ones together under the same roof.
Are there vacation rentals in Islamorada that welcome kids?
With 166 family-friendly vacation rentals to select from in Islamorada, now is a great time to introduce the kiddos to the joys of travel. Simply click on our “Properties good for families” filter to locate stays that feature conveniences perfect for traveling families, like dining rooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Islamorada?
There’s a ton of amazing things to do and see with the family in Islamorada, such as:

  • Theater of the Sea
  • Annes Beach
  • Robbies

Are there one-bedroom vacation rentals in Islamorada?
Islamorada has 16 one-bedroom rentals on offer. Often positioned in popular areas due to their smaller size, a one-bedroom vacation rental is perfect if you’re getting away with your partner or a buddy. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you’ll be able to kick back while discovering this exciting destination.
Can I find two-bedroom vacation rentals in Islamorada?
Take your pick of 57 two-bedroom properties in Islamorada. Settle the kids into the second room or maybe fill it with a couple of your besties. There’s space for whoever’s lucky enough to be coming along for the ride.
Are there vacation rentals with WiFi in Islamorada?
Whether you want to keep up with world events, check emails or surf your social networks, there are 77 vacation homes with WiFi in Islamorada. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Islamorada?
Pick your dates and then make use of our filters to find vacation rentals with air conditioning in Islamorada on Vrbo. With 165 air-conditioned properties available, you can look forward to a cool and comfy break.
How old do you have to be to rent a vacation rental in Islamorada?
It’s a good idea to check with the Islamorada vacation property you’re considering on Vrbo as the minimum age varies. However, normally it’s 16, 18 or 21.
How long can I rent a vacation rental in Islamorada for?
The amount of time you can stay in an Islamorada vacation rental for differs depending on the property. Just put in your dates of travel to browse available options offering longer term stays. They have all the things you need to make your extended trip more convenient and comfortable, such as laundries and air conditioning. Some Vrbo vacation properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.

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