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Islamorada Vacation Rentals

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Recommended Vacation Rentals in Islamorada

Find your perfect vacation rental in Islamorada: from $210 per night

House Islamorada
Dec 12 - Dec 19
House ∙ 14 guests ∙ 6 bedrooms

House

Islamorada, Monroe County, Florida, United States
$1,615
per night
Excellent(18 ratings)
$1,615
per night
View deal
House Islamorada
Oct 19 - Oct 26
House ∙ 10 guests ∙ 5 bedrooms

House

Islamorada, Monroe County, Florida, United States
$2,796
per night
Outstanding(54 ratings)
$2,796
per night
View deal
Resort Islamorada
-76%
Nov 19 - Nov 26
Resort ∙ 127 guests ∙ 2 bedrooms

Cheeca Lodge & Spa

Islamorada, Monroe County, Florida, United States
$1,904$462
per night
Very good
$1,904$462
per night
View deal
House Islamorada
-29%
Feb 8 - Feb 15
House ∙ 14 guests ∙ 7 bedrooms

293 m² House

Islamorada, Monroe County, Florida, United States
$4,380$3,100
per night
Outstanding(66 ratings)
$4,380$3,100
per night
View deal
House Islamorada
-20%
Feb 8 - Feb 15
House ∙ 6 guests ∙ 2 bedrooms

House

Islamorada, Monroe County, Florida, United States
$871$697
per night
Outstanding(29 ratings)
$871$697
per night
View deal
Condo Islamorada
Nov 16 - Nov 23
Condo ∙ 12 guests ∙ 5 bedrooms

208 m² Condo

Islamorada, Monroe County, Florida, United States
$1,226
per night
Outstanding(1 rating)
$1,226
per night
View deal
Condo Islamorada
Dec 21 - Dec 28
Condo ∙ 6 guests ∙ 3 bedrooms

74 m² Condo

Islamorada, Monroe County, Florida, United States
$954
per night
Outstanding(7 ratings)
$954
per night
View deal
House Islamorada
Nov 16 - Nov 23
House ∙ 12 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
$1,516
per night
Outstanding(1 rating)
$1,516
per night
View deal
House Islamorada
Aug 2 - Aug 9
Free cancellation
House ∙ 3 guests ∙ 1 bedroom

House

Islamorada, Monroe County, Florida, United States
$546
per night
Outstanding(2 ratings)
$546
per night
View deal
House Islamorada
-45%
Feb 8 - Feb 15
House ∙ 10 guests ∙ 5 bedrooms

204 m² House

Islamorada, Monroe County, Florida, United States
$3,628$2,013
per night
Outstanding(122 ratings)
$3,628$2,013
per night
View deal
House Islamorada
-26%
Aug 2 - Aug 9
Free cancellation
House ∙ 5 guests ∙ 2 bedrooms

121 m² House

Islamorada, Monroe County, Florida, United States
$924$682
per night
$924$682
per night
View deal
House Islamorada
Feb 8 - Feb 15
House ∙ 10 guests ∙ 5 bedrooms

228 m² House

Islamorada, Monroe County, Florida, United States
$2,781
per night
Outstanding(120 ratings)
$2,781
per night
View deal
House Islamorada
Feb 8 - Feb 15
House ∙ 8 guests ∙ 4 bedrooms

184 m² House

Islamorada, Monroe County, Florida, United States
$1,190
per night
Outstanding(127 ratings)
$1,190
per night
View deal
House Islamorada
Dec 21 - Dec 28
House ∙ 6 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
$768
per night
Outstanding(154 ratings)
$768
per night
View deal
House Islamorada
Feb 8 - Feb 15
House ∙ 10 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
$895
per night
Outstanding(12 ratings)
$895
per night
View deal

Apartments with a balcony or patio

Villa  Islamorada
Mar 15 - Mar 22
$420 per night
Villa ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Islamorada
Mar 15 - Mar 22
$560 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Islamorada
Jan 4 - Jan 11
$2,201 per night
House ∙ 12 guests ∙ 4 bedrooms
4.9
Outstanding(10 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
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Best vacation rentals with a balcony

Condo  Islamorada
Sept 6 - Sept 13
$364 per night
Condo ∙ 4 guests ∙ 1 bedroom
Islamorada, Monroe County, Florida, United States
Balcony
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Cottage  Islamorada
Aug 2 - Aug 9
$385 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
Balcony
View deal
House  Islamorada
Apr 26 - May 3
$1,247 per night
House ∙ 6 guests ∙ 3 bedrooms
Islamorada, Monroe County, Florida, United States
Free cancellation
Balcony
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Vacation rentals with a fireplace

House  Islamorada
Jun 7 - Jun 14
-20%
$2,363
$1,890 per night
House ∙ 8 guests ∙ 3 bedrooms
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
House  Islamorada
Nov 16 - Nov 23
-19%
$1,013
$821 per night
House ∙ 8 guests ∙ 3 bedrooms
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
Apartment  Islamorada
Nov 16 - Nov 23
-59%
$3,415
$1,401 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
See all offers

Best Vacation Home Deals in Islamorada

Save up to 23%

Condo Islamorada
Dec 21 - Dec 28
-8%
$542
$501 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.5
Excellent(45 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
Feb 8 - Feb 15
-8%
$426
$394 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(10 ratings)
Islamorada, Monroe County, Florida, United States
View deal
Condo Islamorada
Feb 8 - Feb 15
-23%
$2,168
$1,662 per night
Condo ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(24 ratings)
Islamorada, Monroe County, Florida, United States
View deal

2,469 beautiful vacation rentals from 18 vacation rental websites are listed in Islamorada, with prices beginning at $210 per night. HomeToGo instantly shows the best offers by comparing all of the listed vacation homes in Islamorada from its various partners.

Budget-friendly Rentals in Islamorada

Find Fantastic yet Inexpensive Rentals

House Islamorada
Apr 5 - Apr 12
$1,943 per night
House ∙ 20 guests ∙ 10 bedrooms
4.9
Outstanding(71 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $873 per night
House ∙ 6 guests ∙ 3 bedrooms
4.4
Very good(18 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $975 per night
House ∙ 8 guests ∙ 5 bedrooms
4.2
Very good(22 ratings)
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
Feb 8 - Feb 15
$973 per night
House ∙ 6 guests ∙ 4 bedrooms
4.8
Outstanding(78 ratings)
Islamorada, Monroe County, Florida, United States
View deal
Condo Islamorada
Feb 8 - Feb 15
$762 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(70 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $531 per night
House ∙ 8 guests ∙ 5 bedrooms
4.7
Excellent(6 ratings)
Islamorada, Monroe County, Florida, United States
View deal

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Popular Rental Amenities in Islamorada

  • Pool (1,794)
  • WiFi (2,400)
  • Pet-friendly (868)
  • Air conditioning (2,407)
  • Kitchen (2,021)
  • Balcony/patio (1,044)
  • Washing machine (1,126)
  • TV (2,196)
  • Fishing (1,578)
  • Dishwasher (1,058)
  • Grill (1,304)
  • Microwave (1,882)

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 7 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 more than 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 August (8/23 – 8/30). During this week, a night will cost on average $1,485. The week with the lowest average prices is in September (9/27 – 10/4).

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 September (9/20 – 9/27). Conversely, it is in December (12/14 – 12/21) 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 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 2,469 rentals
💳 Possible discounts up to 26%
🌙 Nightly prices starting at $210
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 834 homes
🏊 Vacation rentals with pools 1,762 homes
6 reviews
Islamorada vacation rentals have an average rating of 3.7/5 on 6 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Islamorada?

At the moment, there are 2,469 vacation homes from 18 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 34% 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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