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Islamorada Vacation Rentals

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Top 15 Recommended vacation rentals in Islamorada

Find your perfect vacation rental in Islamorada from just $242 per night!

House Islamorada
Aug 31 - Sept 7
House ∙ 8 guests ∙ 4 bedrooms

149 m² House

Islamorada, Monroe County, Florida, United States
$1,065
per night
Outstanding(111 ratings)
$1,065
per night
View deal
Villa Islamorada
Aug 31 - Sept 7
Villa ∙ 6 guests ∙ 2 bedrooms

128 m² Villa

Islamorada, Monroe County, Florida, United States
$573
per night
Outstanding(122 ratings)
$573
per night
View deal
House Islamorada
May 17 - May 24
House ∙ 12 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
$1,502
per night
Excellent(3 ratings)
$1,502
per night
View deal
House Islamorada
May 4 - May 11
House ∙ 8 guests ∙ 4 bedrooms

179 m² House

Islamorada, Monroe County, Florida, United States
$1,107
per night
Outstanding(122 ratings)
$1,107
per night
View deal
Condo Islamorada
May 10 - May 17
Condo ∙ 12 guests ∙ 5 bedrooms

208 m² Condo

Islamorada, Monroe County, Florida, United States
$1,267
per night
Outstanding(3 ratings)
$1,267
per night
View deal
House Islamorada
May 4 - May 11
House ∙ 6 guests ∙ 2 bedrooms

128 m² House

Islamorada, Monroe County, Florida, United States
$570
per night
Outstanding(58 ratings)
$570
per night
View deal
House Islamorada
May 4 - May 11
House ∙ 10 guests ∙ 5 bedrooms

242 m² House

Islamorada, Monroe County, Florida, United States
$856
per night
Excellent(113 ratings)
$856
per night
View deal
House Islamorada
-8%
May 4 - May 11
House ∙ 8 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
$718$662
per night
Outstanding(251 ratings)
$718$662
per night
View deal
House Islamorada
May 4 - May 11
House ∙ 10 guests ∙ 5 bedrooms

242 m² House

Islamorada, Monroe County, Florida, United States
$945
per night
Outstanding(150 ratings)
$945
per night
View deal
House Islamorada
-8%
Feb 21 - Feb 28
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

Islamorada, Monroe County, Florida, United States
$1,458$1,340
per night
Outstanding(71 ratings)
$1,458$1,340
per night
View deal
House Islamorada
-4%
Aug 31 - Sept 7
House ∙ 10 guests ∙ 4 bedrooms

297 m² House

Islamorada, Monroe County, Florida, United States
$1,651$1,587
per night
Outstanding(113 ratings)
$1,651$1,587
per night
View deal
House Islamorada
-8%
May 4 - May 11
House ∙ 10 guests ∙ 3 bedrooms

929 m² House

Islamorada, Monroe County, Florida, United States
$814$752
per night
Outstanding(40 ratings)
$814$752
per night
View deal
House Islamorada
May 4 - May 11
House ∙ 6 guests ∙ 3 bedrooms

149 m² House

Islamorada, Monroe County, Florida, United States
$604
per night
Outstanding(109 ratings)
$604
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
from $887
per night
Very good(24 ratings)
from $887
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
from $383
per night
Excellent(8 ratings)
from $383
per night
View deal

Vacation rentals and apartments with air conditioning

House  Islamorada
from $1,200 per night
House ∙ 12 guests ∙ 5 bedrooms

325 m² House

4.7
Excellent(68 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
View deal
House  Islamorada
from $213 per night
6 guests ∙ 2 bedrooms

House

5.0
Outstanding(4 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
View deal
House  Islamorada
from $632 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(4 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
View deal
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Apartments with a balcony or patio

House  Islamorada
Aug 31 - Sept 7
$1,560 per night
House ∙ 8 guests ∙ 4 bedrooms

204 m² House

5.0
Outstanding(122 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Islamorada
Aug 31 - Sept 7
-7%
$704
$652 per night
House ∙ 6 guests ∙ 2 bedrooms

112 m² House

5.0
Outstanding(202 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
Villa  Islamorada
Mar 14 - Mar 21
$417 per night
Villa ∙ 6 guests ∙ 2 bedrooms

141 m² Villa

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
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Vacation rentals with Wi-Fi

House  Islamorada
from $506 per night
8 guests ∙ 5 bedrooms

House

4.3
Very good(8 ratings)
Islamorada, Monroe County, Florida, United States
Internet
View deal
House  Islamorada
from $555 per night
10 guests ∙ 4 bedrooms

House

4.9
Outstanding(23 ratings)
Islamorada, Monroe County, Florida, United States
Internet
View deal
House  Islamorada
from $717 per night
10 guests ∙ 5 bedrooms

House

5.0
Outstanding(7 ratings)
Islamorada, Monroe County, Florida, United States
Internet
View deal
See all offers

Budget-friendly Rentals in Islamorada

Find Fantastic yet Inexpensive Rentals

House Islamorada
from $589 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $545 per night
House ∙ 8 guests ∙ 5 bedrooms

266 m² House

4.8
Outstanding(9 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $356 per night
12 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
View deal

Top-Rated Offers and Accommodations in Islamorada

Book Vacation Rentals with the Highest User Rating

House Islamorada
from $1,539 per night
House ∙ 14 guests ∙ 6 bedrooms

511 m² House

4.9
Outstanding(76 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $1,853 per night
House ∙ 12 guests ∙ 5 bedrooms

372 m² House

5.0
Outstanding(68 ratings)
Islamorada, Monroe County, Florida, United States
View deal
Condo Islamorada
from $303 per night
6 guests ∙ 4 bedrooms

Condo

4.9
Outstanding(61 ratings)
Islamorada, Monroe County, Florida, United States
View deal

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Popular Rental Amenities in Islamorada

  • Pool (1,775)
  • WiFi (2,375)
  • Pet-friendly (890)
  • Air conditioning (2,329)
  • Kitchen (1,963)
  • Balcony/patio (1,053)
  • Washing machine (1,411)
  • TV (2,145)
  • Fishing (1,547)
  • Dishwasher (953)
  • Grill (1,275)
  • Microwave (1,812)

You will have a large selection of vacation homes to compare and choose from if you are looking for a rental with a pool in Islamorada. Interestingly, our data shows that more hotel room offer a pool than condo. In addition, they can welcome 6 people, on average, while condo with pools can accommodate an average of 5 guests. You can also find and book a vacation rental providing a pool near the water, which is the case for nearly half of the rentals there.

Price and Availability Index in Islamorada

Click on any bar to see price and availability information

Vacation Rental Price Information in Islamorada

The graph shows the average rental prices for the next twelve months in Islamorada. The week with the highest average prices is in December (12/27 – 1/3). During this week, a night will cost on average $938. The week with the lowest average prices is in September (9/13 – 9/20).

Rental availability information in Islamorada

Have a look at the above graph to see the global availability of vacation rentals in Islamorada. The week with the lowest percentage of available vacation rentals is in April (4/11 – 4/18). Conversely, it is in September (9/6 – 9/13) that the highest percentage of vacation homes are available.

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.

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.

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.

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.

Information about vacation rentals in Islamorada

🏡 Vacation rentals available 2,471 rentals
🌙 Nightly prices starting at $242
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 890 homes
🏊 Vacation rentals with pools 1,779 homes
398,408 reviews
Islamorada vacation rentals have an average rating of 4.5/5 on 398,408 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Islamorada?

At the moment, there are 2,471 vacation homes from 16 different providers in Islamorada.

What are the most popular vacation home amenities in Islamorada?

When looking to book a vacation home in Islamorada, the most requested amenities include Pool, Internet, and Pets allowed.

Are there pet-friendly vacation rentals in Islamorada?

If you're travelling with a dog, over 36% of vacation rentals in Islamorada are pet-friendly.

What's the best month to visit Islamorada?

When booking a vacation rental in Islamorada, remember that the rainiest months are usually September and August, with February often being the sunniest.

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