Vacation rentals in Islamorada - HomeToGo base64Hash Vacation rentals in Islamorada - HomeToGo

Vacation rentals in Islamorada

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Top 15 most Recommended Vacation Rentals in Islamorada

Discover your ideal Islamorada vacation rental with real-time comparisons of 1,907 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Cabin Islamorada
Cabin ∙ 6 guests ∙ 2 bedrooms

Fully equipped big cottage with pool, garden & terrace | Nature view | Perfect for remote work | Pets allowed

Islamorada, Monroe County, Florida, United States
from $174
per night
from $174
per night
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House Islamorada
House ∙ 6 guests ∙ 3 bedrooms

House with barbecue, private pool & jacuzzi | Nature view

Islamorada, Monroe County, Florida, United States
from $203
per night
Outstanding(3 ratings)
from $203
per night
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House Islamorada
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with grill, jacuzzi & private pool | Suitable for remote work

Islamorada, Monroe County, Florida, United States
from $348
per night
Outstanding(22 ratings)
from $348
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

Children-friendly vacation home with heated pool, terrace & yard

Islamorada, Monroe County, Florida, United States
from $375
per night
Outstanding(188 ratings)
from $375
per night
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House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with heated pool & barbeque | Nature view | Good for workation

Islamorada, Monroe County, Florida, United States
from $174
per night
from $174
per night
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House Islamorada
House ∙ 9 guests ∙ 4 bedrooms

Vacation home with pool, patio & garden | Perfect for remote work

Islamorada, Monroe County, Florida, United States
from $313
per night
Outstanding(26 ratings)
from $313
per night
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House Islamorada
House ∙ 12 guests ∙ 5 bedrooms

Children-friendly wonderful vacation home with garden, private pool & patio | Nature view | Pet-friendly

Islamorada, Monroe County, Florida, United States
from $1,483
per night
Outstanding(97 ratings)
from $1,483
per night
View deal
House Islamorada
House ∙ 18 guests ∙ 9 bedrooms

Family-friendly house with garden, patio & private pool | Good for workation

Islamorada, Monroe County, Florida, United States
from $2,366
per night
from $2,366
per night
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House Islamorada
House ∙ 14 guests ∙ 6 bedrooms

House with barbeque, patio & private pool | Nature view | Perfect for remote work

Islamorada, Monroe County, Florida, United States
from $2,376
per night
Outstanding(57 ratings)
from $2,376
per night
View deal
House Islamorada
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with private pool, yard & terrace | Nature view

Islamorada, Monroe County, Florida, United States
from $1,124
per night
Outstanding(76 ratings)
from $1,124
per night
View deal
Condo Islamorada
Condo ∙ 3 guests ∙ 1 bedroom

Family-oriented charming condo with grill, heated pool & patio | Nature view

Islamorada, Monroe County, Florida, United States
from $135
per night
from $135
per night
View deal
Condo Islamorada
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with jacuzzi, grill & patio | Nature view

Islamorada, Monroe County, Florida, United States
from $183
per night
Outstanding(59 ratings)
from $183
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped house with BBQ | Nature view | Pets are welcome

Islamorada, Monroe County, Florida, United States
from $320
per night
Very good(2 ratings)
from $320
per night
View deal
House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly charming house with terrace, hot tub & private pool | Perfect for remote work | Pets allowed

Islamorada, Monroe County, Florida, United States
from $466
per night
Outstanding(14 ratings)
from $466
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 3 bedrooms

House with barbecue & private pool

Islamorada, Monroe County, Florida, United States
from $380
per night
from $380
per night
View deal

Vacation rentals and apartments with air conditioning

Apartment  Islamorada
from $113
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment with 1 room for 2 persons

Islamorada, Monroe County, Florida, United States
Air conditioning
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Apartment  Islamorada
from $200
per night
Apartment ∙ 10 guests ∙ 3 bedrooms

Children-friendly lovely rental apartment with private pool, terrace & garden

5.0
Outstanding(33 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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House  Islamorada
from $181
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped ample vacation home with patio | Pet-friendly

5.0
Outstanding(1 rating)
Islamorada, Monroe County, Florida, United States
Air conditioning
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Vacation houses with Balconies or Patios

House  Islamorada
from $176
per night
House ∙ 9 guests ∙ 2 bedrooms

Family-oriented nice vacation home with garden, BBQ & patio | Nature view

4.5
Excellent(7 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
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House  Islamorada
from $383
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly lovely house with garden, terrace & BBQ | Pets allowed

5.0
Outstanding(16 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
View deal
Villa  Islamorada
from $1,863
per night
Villa ∙ 10 guests ∙ 5 bedrooms

Villa with grill, terrace & private pool | Nature view

5.0
Outstanding(4 ratings)
Islamorada, Monroe County, Florida, United States
Balcony/Patio
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Vacation Rentals With Fireplaces

House  Islamorada
from $1,452
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with private pool, yard & barbeque

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
House  Islamorada
from $587
per night
House ∙ 5 guests ∙ 2 bedrooms

Family-friendly charming house with heated pool, garden & jacuzzi | Pet-friendly

5.0
Outstanding(114 ratings)
Islamorada, Monroe County, Florida, United States
Fireplace
View deal
Condo  Islamorada
from $191
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, garden & heated pool | Nature view

Islamorada, Monroe County, Florida, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Islamorada offering exceptional value for money

House Islamorada
from $277
per night
House ∙ 4 guests ∙ 2 bedrooms

House with grill & private pool | Perfect for remote work

4.8
Outstanding(47 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $237
per night
House ∙ 6 guests ∙ 3 bedrooms

House with grill, yard & patio | Nature view | Good for workation

Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $545
per night
House ∙ 6 guests ∙ 1 bedroom

Charming vacation home | Pets are welcome

Islamorada, Monroe County, Florida, United States
View deal

Top-Rated Vacation rentals in Islamorada

Book the highest-rated Islamorada vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Condo Islamorada
from $127
per night
Condo ∙ 3 guests ∙ 1 bedroom

Family-friendly condo with hot tub, barbeque & heated pool | Water view

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $341
per night
House ∙ 4 guests ∙ 2 bedrooms

House with pool

5.0
Outstanding(12 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $427
per night
House ∙ 6 guests ∙ 2 bedrooms

House with heated pool, garden & terrace

5.0
Outstanding(99 ratings)
Islamorada, Monroe County, Florida, United States
View deal

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Popular Features & Amenities in Islamorada

  • Pool (1,545)
  • Pet-friendly (763)
  • Fishing (1,292)
  • Air conditioning (1,824)
  • Balcony/patio (999)
  • Kitchen (1,362)
  • WiFi (1,809)
  • TV (1,708)
  • Washing machine (943)
  • Grill (1,099)
  • Microwave (1,329)
  • Dishwasher (856)

You can find a large selection of accommodations to book if you are looking for an accommodation including a pool in Islamorada. Interestingly, our data shows that more hotel room provide a pool than condo. In addition, they can host 5 vacationers, on average, while condo with pools can accommodate an average of 5 people. more than half of Islamorada's rentals offering a pool are within two miles of water, divide your time between the pool and the waterfront

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 average prices of rentals in Islamorada for the upcoming twelve months. The most expensive prices are in February (2/14 – 2/21). Prices reach an average of $662 per night. You can find the most affordable prices on accommodations in November. Prices during that period are typically $577 per night on average.

Rental availability information in Islamorada

The graph shows the weekly availability rate in Islamorada for the upcoming twelve months. Be careful if you plan to go to Islamorada in November, as it comprises the busiest week of the next 12 months (11/7 – 11/14). December (12/6 – 12/13) has got the highest percentage of available rentals.

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 1,907 rentals
🌙 Nightly prices starting at $129
⭐ Popular amenities Pool, Pets allowed and Fishing
🐾 Pet friendly homes 765 homes
🏊 Vacation rentals with pools 1,563 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 price per night for a vacation rental in Islamorada?

The price of a night's stay in Islamorada starts at $129. Average prices for house rentals are $747 per night. Condos in Islamorada cost $400 per night on average.

How many vacation rentals are available to book in Islamorada?

There are currently 1,907 vacation homes from 21 providers in Islamorada.

What are the most popular amenities for vacation rentals in Islamorada?

Usually travelers look for Pool, Pets allowed, and Fishing when booking a vacation rental in Islamorada.

How many vacation homes with a pool are there in Islamorada?

Browse 1,563 vacation rentals available to book in Islamorada.

Are pets allowed in vacation homes in Islamorada?

In case if you are traveling with a pet in Islamorada - 40% of vacation homes allow pets.

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