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Islamorada Vacation Rentals

Find 1,875 available home rentals from 19 partners
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Top 15 Recommended vacation rentals in Islamorada

Find your perfect vacation rental in Islamorada from just $141 per night!

House Islamorada
House ∙ 10 guests ∙ 5 bedrooms

316 m² House

Islamorada, Monroe County, Florida, United States
from $1,479
per night
Outstanding(28 ratings)
from $1,479
per night
View deal
Condo Islamorada
Condo ∙ 3 guests ∙ 1 bedroom

Condo

Islamorada, Monroe County, Florida, United States
from $185
per night
from $185
per night
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Condo Islamorada
Condo ∙ 6 guests ∙ 3 bedrooms

Condo

Islamorada, Monroe County, Florida, United States
from $300
per night
Outstanding(59 ratings)
from $300
per night
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House Islamorada
House ∙ 12 guests ∙ 5 bedrooms

372 m² House

Islamorada, Monroe County, Florida, United States
from $2,082
per night
Outstanding(97 ratings)
from $2,082
per night
View deal
House Islamorada
House ∙ 9 guests ∙ 2 bedrooms

133 m² House

Islamorada, Monroe County, Florida, United States
from $248
per night
Excellent(7 ratings)
from $248
per night
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House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

House

Islamorada, Monroe County, Florida, United States
from $411
per night
from $411
per night
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House Islamorada
House ∙ 8 guests ∙ 3 bedrooms

149 m² House

Islamorada, Monroe County, Florida, United States
from $510
per night
Outstanding(16 ratings)
from $510
per night
View deal
House Islamorada
House ∙ 12 guests ∙ 4 bedrooms

325 m² House

Islamorada, Monroe County, Florida, United States
from $439
per night
Excellent(6 ratings)
from $439
per night
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House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

House

Islamorada, Monroe County, Florida, United States
from $253
per night
from $253
per night
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House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
from $322
per night
from $322
per night
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House Islamorada
House ∙ 8 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
from $817
per night
(2 ratings)
from $817
per night
View deal
Apartment Islamorada
Apartment ∙ 2 guests ∙ 1 bedroom

37 m² Apartment

Islamorada, Monroe County, Florida, United States
from $141
per night
Outstanding(6 ratings)
from $141
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

House

Islamorada, Monroe County, Florida, United States
from $820
per night
Outstanding(36 ratings)
from $820
per night
View deal
House Islamorada
House ∙ 11 guests ∙ 4 bedrooms

173 m² House

Islamorada, Monroe County, Florida, United States
from $893
per night
Outstanding(1 rating)
from $893
per night
View deal
House Islamorada
House ∙ 14 guests ∙ 6 bedrooms

437 m² House

Islamorada, Monroe County, Florida, United States
from $3,251
per night
Outstanding(72 ratings)
from $3,251
per night
View deal

Vacation rentals and apartments with air conditioning

Apartment  Islamorada
from $296 per night
Apartment ∙ 10 guests ∙ 3 bedrooms

372 m² Apartment

5.0
Outstanding(33 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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House  Islamorada
from $222 per night
House ∙ 6 guests ∙ 2 bedrooms

130 m² House

5.0
Outstanding(18 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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House  Islamorada
from $911 per night
House ∙ 8 guests ∙ 4 bedrooms

House

5.0
Outstanding(30 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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Best vacation rentals with a balcony

House  Islamorada
from $432 per night
House ∙ 6 guests ∙ 2 bedrooms

House

5.0
Outstanding(154 ratings)
Islamorada, Monroe County, Florida, United States
Balcony
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House  Islamorada
from $335 per night
House ∙ 4 guests ∙ 2 bedrooms

106 m² House

5.0
Outstanding(14 ratings)
Islamorada, Monroe County, Florida, United States
Balcony
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House  Islamorada
from $589 per night
House ∙ 6 guests ∙ 3 bedrooms

130 m² House

4.8
Outstanding(103 ratings)
Islamorada, Monroe County, Florida, United States
Balcony
View deal
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Apartments with a balcony or patio

House  Islamorada
from $658 per night
House ∙ 8 guests ∙ 2 bedrooms

186 m² House

5.0
Outstanding(111 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Islamorada
from $817 per night
House ∙ 6 guests ∙ 3 bedrooms

House

5.0
Outstanding(5 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
House  Islamorada
from $1,326 per night
House ∙ 8 guests ∙ 3 bedrooms

177 m² House

5.0
Outstanding(48 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
See all offers

Budget-friendly Rentals in Islamorada

Find Fantastic yet Inexpensive Rentals

House Islamorada
from $547 per night
House ∙ 6 guests ∙ 2 bedrooms

129 m² House

5.0
Outstanding(188 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $1,291 per night
House ∙ 10 guests ∙ 5 bedrooms

269 m² House

5.0
Outstanding(34 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $1,585 per night
House ∙ 16 guests ∙ 5 bedrooms

511 m² House

4.9
Outstanding(91 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
from $1,031 per night
House ∙ 8 guests ∙ 4 bedrooms

314 m² House

5.0
Outstanding(53 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $448 per night
House ∙ 4 guests ∙ 2 bedrooms

88 m² House

4.8
Outstanding(50 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $542 per night
House ∙ 6 guests ∙ 2 bedrooms

129 m² House

4.9
Outstanding(47 ratings)
Islamorada, Monroe County, Florida, United States
View deal

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Popular Rental Amenities in Islamorada

  • Pool (1,553)
  • WiFi (1,812)
  • Pet-friendly (743)
  • Air conditioning (1,816)
  • Kitchen (1,348)
  • Balcony/patio (964)
  • Washing machine (925)
  • TV (1,689)
  • Fishing (1,310)
  • Dishwasher (872)
  • Grill (1,105)
  • Microwave (1,349)

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 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 February (2/14 – 2/21). During this week, a night will cost on average $907. The week with the lowest average prices is in January (1/10 – 1/17).

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 November (11/14 – 11/21). Conversely, it is in June (6/20 – 6/27) 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 1,875 rentals
🌙 Nightly prices starting at $141
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 742 homes
🏊 Vacation rentals with pools 1,556 homes
5 reviews
Islamorada vacation rentals have an average rating of 3.8/5 on 5 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Islamorada?

At the moment, there are 1,875 vacation homes from 19 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 40% 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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