Islamorada holiday lettings

We found 2,135 holiday rentals — enter your dates for availability

Select from 590 houses, 84 apartments and other holiday rentals to find the perfect place for your stay in Islamorada. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as a pool and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent for 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, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Travel to relaxing Islamorada

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

Sightseeing in and around Islamorada

Are you looking for attractions to see during your stay? Travellers enjoy fun activities like fishing and diving. Venture out of your cosy holiday rental and experience everything that Islamorada has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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

Travellers appreciate the beautiful ocean views and breathtaking sunsets, which is just a taste of what Islamorada has to offer. Whether you're an outdoor enthusiast or just want to take in the scenery, Islamorada is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Islamorada

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

Frequently asked questions

What is the best area to stay in Islamorada when booking a holiday 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 holiday rental here that’s just right for you.
What is the most popular type of holiday rental accommodation in Islamorada?
Houses are the most popular style of holiday rental in Islamorada, according to our data. Even if you have a different idea about what you want, Vrbo has holiday homes in loads of sizes and shapes. Filter our options to find your perfect fit.
How much does it cost to rent a holiday rental in Islamorada?
Season, property type and length of stay are some things that can influence the price of a holiday home. Simply add your dates of travel to find your ideal escape. From homey country cottages to expansive villas, all Vrbo holiday 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 holiday 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 holiday 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 holiday 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 holiday rentals have the best amenities for chilling out with the people you cherish the most.
Are there large group holiday rentals in Islamorada?
You can pick from 18 holiday properties in Islamorada that can host a group of 10 or more guests. Whether you’re organising 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 holiday rentals in Islamorada that welcome kids?
With 166 family-friendly holiday 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 travelling 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:

  • Theatre of the Sea
  • Annes Beach
  • Robbies

Are there one-bedroom holiday rentals in Islamorada?
Islamorada has 16 one-bedroom rentals on offer. Often positioned in popular areas due to their smaller size, a one-bedroom holiday 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 holiday 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 holiday rentals with WiFi in Islamorada?
Whether you want to keep up with world events, check emails or surf your social networks, there are 77 holiday homes with WiFi in Islamorada. Check the “WiFi” box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Islamorada?
Pick your dates and then make use of our filters to find holiday 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 holiday rental in Islamorada?
It’s a good idea to check with the Islamorada holiday 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 holiday rental in Islamorada for?
The amount of time you can stay in an Islamorada holiday 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 holiday properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.

Explore destinations around Islamorada

People also search for

Naples Apartments
Standard Link for Naples
Sarasota Villas
Standard Link for Sarasota
Fort Myers Villas
Standard Link for Fort Myers
Daytona Beach Apartments
Standard Link for Daytona Beach
Naples Villas
Standard Link for Naples
Davenport Villas
Standard Link for Davenport

More Holiday Rentals ideas

Sarasota Holiday Rentals
Standard Link for Sarasota
Davenport Holiday Rentals
Standard Link for Davenport
Fort Myers Beach Holiday Rentals
Standard Link for Fort Myers Beach
Vero Beach Holiday Rentals
Standard Link for Vero Beach
Key West Holiday Rentals
Standard Link for Key West
Daytona Beach Holiday Rentals
Standard Link for Daytona Beach
Destin Holiday Rentals
Standard Link for Destin
Cape Coral Holiday Rentals
Standard Link for Cape Coral
West Palm Beach Holiday Rentals
Standard Link for West Palm Beach
Fort Myers Holiday Rentals
Standard Link for Fort Myers
Marco Island Holiday Rentals
Standard Link for Marco Island
Palm Beach Holiday Rentals
Standard Link for Palm Beach
Longboat Key Holiday Rentals
Standard Link for Longboat Key
Key Largo Holiday Rentals
Standard Link for Key Largo
St. Augustine Holiday Rentals
Standard Link for St. Augustine
Naples Holiday Rentals
Standard Link for Naples
Pensacola Beach Holiday Rentals
Standard Link for Pensacola Beach
The Villages Holiday Rentals
Standard Link for The Villages
Cocoa Beach Holiday Rentals
Standard Link for Cocoa Beach
Bradenton Holiday Rentals
Standard Link for Bradenton
Boca Raton Holiday Rentals
Standard Link for Boca Raton
Siesta Key Holiday Rentals
Standard Link for Siesta Key
Venice Holiday Rentals
Standard Link for Venice
Marathon Holiday Rentals
Standard Link for Marathon