Islamorada Vacation Rentals

Compare 662 available properties from 14 providers
Islamorada
Anytime
2 guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Boat
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
Save up to 25%

Best Vacation Home Deals in Islamorada

Condo Islamorada
-25%
Apr. 17 - Apr. 24
Condo ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $335 $446
FloridaRentals.com
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Discover a vacation home meeting your expectations among the 662 welcoming options from 14 providers in Islamorada. Using HomeToGo you can instantly search and compare the prices of each available property to discover the best deal and save up to 25%.

Recommended Vacation Rentals in Islamorada

Find your perfect vacation rental in Islamorada: from $122 per night

Condo Islamorada 4
-15%
Nov. 28 - Dec. 5
Condo ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $377 $446
FloridaRentals.com
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Apartment Islamorada 6
Apartment ∙ 6 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $315
Vrbo
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House Islamorada 4
House ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $356
Vrbo
5.0/5.0
"Excellent"
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House Islamorada 6
House ∙ 6 guests ∙ 3 bedrooms
Islamorada, Monroe County, Florida, United States
from $362
Vrbo
5.0/5.0
"Excellent"
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House Islamorada 6
House ∙ 6 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $254
Vrbo
4.9/5.0
"Excellent"
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House Islamorada 4
-15%
Apr. 17 - Apr. 24
House ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $250 $295
Vrbo
4.8/5.0
"Excellent"
View deal
Apartment Islamorada 5
-32%
Nov. 6 - Nov. 13
Apartment ∙ 5 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $259 $380
Vrbo
4.7/5.0
"Outstanding"
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House Islamorada 4
House ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $310
Vrbo
5.0/5.0
"Excellent"
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Apartment Islamorada 4
Apartment ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $243
Vrbo
4.7/5.0
"Outstanding"
View deal
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Vacation rentals with Wi-Fi

House Internet Islamorada
-34%
May 15 - May 22
Internet
House ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $498 $751
Vrbo
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House Internet Islamorada
Internet
House ∙ 6 guests ∙ 3 bedrooms
Islamorada, Monroe County, Florida, United States
from $627
Vrbo
5.0/5.0
"Excellent"
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House Internet Islamorada
Internet
House ∙ 6 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $390
Vrbo
5.0/5.0
"Excellent"
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Vacation rentals and apartments with air conditioning

Apartment Aircondition Islamorada
Aircondition
Apartment ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $375
Vrbo
4.8/5.0
"Excellent"
View deal
Apartment Aircondition Islamorada
Aircondition
Apartment ∙ 5 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $289
Vrbo
4.8/5.0
"Excellent"
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House Aircondition Islamorada
Aircondition
House ∙ 4 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
from $341
Vrbo
4.9/5.0
"Excellent"
View deal
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Apartments and vacation rentals with a kitchen

Apartment Kitchen Islamorada
Kitchen
Apartment ∙ 4 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
from $383
Vrbo
5.0/5.0
"Excellent"
View deal
House Kitchen Islamorada
Kitchen
House ∙ 4 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
from $360
Vrbo
5.0/5.0
"Excellent"
View deal
House Kitchen Islamorada
Kitchen
House ∙ 6 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
from $309
Vrbo
5.0/5.0
"Excellent"
View deal
See all offers

Popular Rental Amenities in Islamorada

  • Internet (449)
  • Kitchen (443)
  • Parking (430)
  • Air conditioning (382)
  • TV (375)
  • No smoking (361)
  • Microwave (360)
  • Grill (350)
  • Dishwasher (312)
  • Washer (293)
  • Fishing (246)
  • Pool (244)

Check above for the most selected filters in Islamorada and the number of vacation rentals that offer them. Many properties in Islamorada offer "TVs" or "internet," which makes it a wonderful vacation destination if you want to tune out with some TV time or you can't imagine a vacation without internet. You could even look for rentals if you like to end your days curled up by the fire (39 rentals include "fireplaces" in Islamorada) or if you love sweating the stress away in saunas (26 rentals in Islamorada include "saunas").

The Weather in Islamorada

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- Rainy days

Find the Islamorada climate diagram. On average, the warmest month is July. On the contrary, the coolest month is February. The rainiest month is September while the driest month is February.

Accommodations for your vacation in Islamorada

In Islamorada, more than half of the 662 vacation properties are house rentals, which represent 54.19% of its listed properties. Additionally, the average nightly price of house rentals there is $824, and the median size is 201 m². Furthermore, these accommodations are perfect for large groups, as most can accommodate 8 guests. If you would prefer to compare another accommodation type, you may want to check apartment rentals, which are the second most frequent accommodation type in Islamorada. The average size of apartment rentals in Islamorada is 113 m², and the average price is $393 per night.

Enjoy an idylic beach vacation at your Islamorada vacation home

Islamorada was where back country sport fishing and salt water fly fishing first burst onto the scene. The 'fishing capital of the world' also has the world's highest density of professional offshore charter boats. Islamorada, which means "purple isles," is also a popular wedding destination, thanks to its raw beauty and crystal blue waters. There's much happening here, from exciting fishing activities to art walks and romantic seaside cafés. Book your Islamorada vacation rental to see what's in store.

Show all 662 properties
How to get to Islamorada?

Flying into Islamorada

The easiest way to reach Islamorada is via the Miami International Airport. From here, take a shuttle bus or taxi to reach your vacation rental on Islamorada.. Alternately, travelers also fly into the Ft. Lauderdale-Hollywood International Airport and the Florida Keys Marathon Airport, which is 45-minutes from Islamorada.

Where to find the best food in Islamorada?

Cuisine of Islamorada

Seafood enthusiasts won't be disappointed with Islamorada's culinary offerings. Choose from fresh-off-the-nets seafood served in all kinds of settings — tiki-covered huts, marina-facing fish houses, beachfront cafés or romantic, secluded bistros. The waterfront is dotted with restaurants, serving everything from Mediterranean cuisine, sushi, organic salads, sandwiches and meatball subs.

Enjoy dinner and live entertainment at the waterfront cafés that serve excellent seafood: there's fried oysters, peel-and-eat-shrimp, and fish sandwiches galore. For the "freshest sushi in all the Keys!" and a hefty beer, wine and sake list, Kaiyo Grill & Sushi does the trick. Don't forget to pack some takeaway to feast on when you return to your Islamorada vacation rental.

What is the weather like in Islamorada?

The weather in Islamorada

The best time to visit is between December and May, when outdoor activities can be enjoyed under sunny, blue skies. Your vacation home in Islamorada should be booked in advance during this peak season. For those who prefer some peace and quiet, as well as discounted prices on rentals, October and November is a great time to visit.

What are the top sights in Islamorada?

The must-see sights of Islamorada

Most people come to Islamorada for its scenery and sunsets. The sea facing restaurants are perfectly aligned to allow diners gorgeous views of the sun sinking into the ocean. From the Islamorada Fist Company restaurant, you can watch sharks being fed while you enjoy your evening meal, as the event usually takes place around sunset. It's also quite possible to enjoy the sunset from the privacy of your sea-facing vacation rental on Islamorada.

Enjoy tropical evenings with relaxed music at the waterfront ICE Amphitheater, housed inside Islamorada Founders Park. This pet-friendly park also features an Olympic-sized pool, ball fields, a shallow water beach, water sports rentals and a skate park. Casa Mar Village meanwhile, is recommended for its local fish market, waterfront shopping and outdoor adventure sports activities. The kids will enjoy hand-feeding giant silver tarpons at Robbie's Marina. Then take them to a fun dolphin, sea lion and parrot show at Theater of the Sea marine mammal park.

What are the best places to discover the arts and culture of Islamorada?

Art and culture on Islamorada

The Coral Shores Performing Arts Center delights audiences with its top-notch productions. Meanwhile the monthly Third Thursday Art Walk organized by the Morada Way Arts & Cultural District is a great way to get acquainted with the town's art spaces and boutiques. The event brings together artisans, sculptors, jewelers, photographers and travelers who enjoy the artist receptions, music, sunsets and other fun activities.

The Jannette De Llanos Art Gallery showcases oil paintings and graphic art of the Florida Keys & beyond, while the Pasta Pantaleo Signature Gallery houses Pasta's sportfish paintings that are vivid and rich in their color schemes. For a look at the artworks of local photographers, painters, sculptors, and mixed media artists, visit Gallery at Ocean Sotheby's International Realty. Lastly, there's Crane Point Museum & Nature Center which regales visitors with its interpretative displays of marine life, local wildlife and exhibits.

Where are the unique attractions in Islamorada?

Excursions and day trips beyond Islamorada

Islamorada boasts rare and extraordinary brimming patch reefs, which is good news for divers. An hour south from your vacation home on Islamorada, lies the Bahia Honda State Park where oceanside camping is possible. Enjoy kayaking, fishing, biking, and snorkeling among other great activities. Take time off to explore Islamorada's colorful shallow coral reefs, its shipwrecks, and an interesting underwater hub for scientific research, called the Aquarius.

Pickles Reef is perfect to spot flamingo tongue cowries and banded coral shrimps. Bud n' Mary's is another popular marina known for its sportfishing shows, chartered fishing expeditions, pontoon boats, and deli's serving excellent coffee by the sea. End the day by retiring back at your sea facing Islamorada vacation rental.

Legendary authors such as Ernest Hemingway have been inspired right here in Islamorada! Come over with the family and book your vacation rental on Islamorada today. The isles are waiting.

What are the must-see attractions in Islamorada?

Incredible Islamorada

Lobster Trap Art Gallery

The vivid artworks at this exciting gallery will ensnare your gaze just like the lobsters in the traps outside its doors.

The Rain Barrel Artisan Village

The perfect day out involves exploring this picturesque artists' village, where there are any number of craft workshops to get involved in, plus exquisite art to discover and take home. Jewellery, sculpture and fine art are just the start.

Florida Keys Brewing Company

This family run microbrewery is a delight, and is ideally situated in the arts and cultural district of town. Enjoy tours, talks and of course, tastings.

History of Diving Museum

A trip to Florida isn't complete without exploring the ocean. Learn about the technical and historical aspects of this pastime through oral exhibits and artefacts found beneath the waves.

Theater of the Sea

Live the dream and swim with Flipper at this incredible center, dedicated to marine life. Seals, dolphins and parrots perform in mesmerising sealife shows.

We compare more than 1,300 providers, including:

Booking.com Vacation Rentals in Islamorada TripAdvisor Vacation Rentals in Islamorada Vrbo Vacation Rentals in Islamorada Airbnb Vacation Rentals in Islamorada Novasol Vacation Rentals in Islamorada Inter Chalet Vacation Rentals in Islamorada EveryStay Vacation Rentals in Islamorada Interhome Vacation Rentals in Islamorada 9flats.com Vacation Rentals in Islamorada HouseTrip Vacation Rentals in Islamorada Belvilla Vacation Rentals in Islamorada Sykes Cottages Vacation Rentals in Islamorada Homestay.com Vacation Rentals in Islamorada Ski Planet Vacation Rentals in Islamorada Only-apartments Vacation Rentals in Islamorada James Villa Holidays Vacation Rentals in Islamorada

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