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Islamorada Vacation Rentals

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Islamorada
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Price per night
Up to $100
$100 - $199
From $200
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Distance to center
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Rating
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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.

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Best Vacation Home Deals in Islamorada

Save up to 44%

House Islamorada
Oct 14 - Oct 21
-44%
$782
$439 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Islamorada with Grill & Yard + Great Views
4.6
"Outstanding" (65 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Oct 14 - Oct 21
-38%
$864
$538 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Yard, Pool & Grill
4.9
"Excellent" (49 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Dec 2 - Dec 9
-42%
$760
$438 per night
House ∙ 9 guests ∙ 4 bedrooms
Vacation Home in Islamorada with Pool, Yard & Grill
4.8
"Excellent" (16 ratings)
Islamorada, Monroe County, Florida, United States
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Discover a vacation rental that matches your criteria among the 1,733 fantastic vacation rentals from different vacation rental websites in Islamorada. Using HomeToGo's search feature you can immediately search and compare the prices of each available rental to discover the best deal and save up to 44%.

Top-Rated Offers and Accommodations in Islamorada

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House Islamorada
Oct 12 - Oct 19
$1,211 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Islamorada with Pool & Grill
4.8
"Excellent" (52 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Oct 12 - Oct 19
-21%
$623
$491 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Islamorada with Ocean Pool + Ocean Views
5.0
"Excellent" (31 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Oct 21 - Oct 28
$508 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Islamorada with Pool & Grill
5.0
"Excellent" (21 ratings)
Islamorada, Monroe County, Florida, United States
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Recommended Vacation Rentals in Islamorada

Find your perfect vacation rental in Islamorada: from $193 per night

Condo Islamorada
Jun 29 - Jul 6
-27%
$585
$426 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Pool & Patio
4.8
"Excellent" (180 ratings)
Islamorada, Monroe County, Florida, United States
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Villa Islamorada
Dec 16 - Dec 23
$403 per night
Villa ∙ 4 guests ∙ 1 bedroom
Villa in Islamorada with Yard & Grill
4.9
"Excellent" (110 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Oct 14 - Oct 21
-40%
$1,006
$599 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Electric Fireplace + Ocean Views
5.0
"Excellent" (155 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Oct 12 - Oct 19
$1,084 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Islamorada with Pool & Grill + Waterfront Views
4.9
"Excellent" (82 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Oct 14 - Oct 21
-44%
$782
$439 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Islamorada with Grill & Yard + Great Views
4.6
"Outstanding" (65 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Oct 12 - Oct 19
-38%
$864
$538 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Yard, Pool & Grill
4.9
"Excellent" (49 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Oct 12 - Oct 19
$278 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Islamorada with Grill, Pool & Yard
4.9
"Excellent" (36 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Dec 16 - Dec 23
$459 per night
Condo ∙ 7 guests ∙ 3 bedrooms
Condo in Islamorada with Yard & Pool + Fantastic View
4.9
"Excellent" (19 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Dec 2 - Dec 9
-42%
$760
$438 per night
House ∙ 9 guests ∙ 4 bedrooms
Vacation Home in Islamorada with Pool, Yard & Grill
4.8
"Excellent" (16 ratings)
Islamorada, Monroe County, Florida, United States
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Budget-friendly Rentals in Islamorada

Find Fantastic yet Inexpensive Rentals

Condo Islamorada
Oct 12 - Oct 19
$393 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in Islamorada with Large Pool
4.7
"Outstanding" (83 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jan 6 - Jan 13
-41%
$976
$575 per night
House ∙ 4 guests ∙ 2 bedrooms
Lovely House in Islamorada with Olympic-Sized Pool + Ocean View
5.0
"Excellent" (180 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Dec 9 - Dec 16
-21%
$938
$738 per night
House ∙ 8 guests ∙ 4 bedrooms
Lovely House in Islamorada with Pool & Grill
4.9
"Excellent" (78 ratings)
Islamorada, Monroe County, Florida, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Islamorada and book a vacation rental with air conditioning.

Condo Air conditioning Islamorada
Aug 26 - Sept 2
-35%
$564
$368 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Rental Condo in Islamorada with Outdoor Pool + Spectacular Views
4.8
"Excellent" (141 ratings)
Islamorada, Monroe County, Florida, United States
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Cottage Air conditioning Islamorada
Jul 29 - Aug 5
$399 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Islamorada with Grill + Ocean Views
5.0
"Excellent" (120 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Air conditioning Islamorada
Oct 12 - Oct 19
$616 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Islamorada with Pool, Yard & Grill + Ocean View
5.0
"Excellent" (66 ratings)
Islamorada, Monroe County, Florida, United States
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Apartments with a balcony or patio

Looking for a home with a balcony? Check out these vacation homes in Islamorada with their own private patios and balconies.

House Balcony/Patio Islamorada
Dec 2 - Dec 9
$697 per night
House ∙ 8 guests ∙ 2 bedrooms
Whole House in Islamorada with Grill & Yard + Spectacular View
5.0
"Excellent" (98 ratings)
Islamorada, Monroe County, Florida, United States
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House Balcony/Patio Islamorada
Oct 12 - Oct 19
-17%
$1,935
$1,601 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Islamorada with Pool, Yard & Grill
5.0
"Excellent" (70 ratings)
Islamorada, Monroe County, Florida, United States
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House Balcony/Patio Islamorada
Apr 6 - Apr 13
$779 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Islamorada with Pool, Grill & Yard
4.7
"Outstanding" (88 ratings)
Islamorada, Monroe County, Florida, United States
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Islamorada accommodation with high-speed internet.

House Internet Islamorada
$304 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Islamorada with Beautiful Pool
5.0
"Excellent" (15 ratings)
Islamorada, Monroe County, Florida, United States
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House Internet Islamorada
$996 per night
House ∙ 6 guests ∙ 3 bedrooms
Lovely House in Islamorada with Grill & Pool + Sunrise View
4.9
"Excellent" (67 ratings)
Islamorada, Monroe County, Florida, United States
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Apartment Internet Islamorada
$136 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Apartment in Key Largo + Water Views
5.0
"Excellent" (24 ratings)
Islamorada, Monroe County, Florida, United States
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Popular Rental Amenities in Islamorada

  • Pool (1,424)
  • WiFi (1,624)
  • Pet-friendly (385)
  • Air conditioning (1,509)
  • Kitchen (1,261)
  • Parking (32)
  • Balcony/patio (555)
  • Washing machine (847)
  • TV (1,523)
  • Fishing (1,125)
  • Dishwasher (779)
  • Grill (934)

Finding a vacation rental with a pool shouldn't be too hard in Islamorada. Most of the vacation rentals have one. In addition, more hotel room include a pool than condo. On average, hotel room with pools in Islamorada accommodate 6 people and have an average cost of $1,059 per night. Among these offers, 72 of them are situated within 2 kilometres of water.

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. Prices rise in December and reach an average of $988 a night (12/23 - 12/30), making it the most expensive time to book a rental in the next 12 months. Prices decrease in September to an average of $566 per night (9/30 - 10/7).

Rental availability information in Islamorada

The availability graph shows the percentage of available rentals in Islamorada. It is harder to find an accommodation during a week of August (8/31 - 9/7), as 85% of the rentals are booked. The week with the most available rentals is in September (9/30 - 10/7), with 73% of the vacation rentals available.

The Weather in Islamorada

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27°
21°
7 days 7
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26°
20°
6 days 6
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27°
21°
7 days 7
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30°
24°
6 days 6
max.
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31°
25°
9 days 9
max.
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32°
26°
12 days 12
max.
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33°
27°
13 days 13
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33°
27°
14 days 14
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32°
26°
16 days 16
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30°
24°
11 days 11
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27°
22°
9 days 9
max.
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26°
21°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. July is the warmest month in Islamorada with average maximum temperatures of 33°. Conversely, February is the coolest month in Islamorada, with temperatures going under 20° According to the climate diagram, September is the rainiest month of the year in Islamorada.

7-Day Weather Forecast in Islamorada

Sun., 24 Sep.
28°
27°

15%

3 h

18 km/h

Mon., 25 Sep.
29°
28°

10%

10 h

12 km/h

Tue., 26 Sep.
29°
29°

0%

10 h

12 km/h

Wed., 27 Sep.
29°
29°

5%

5 h

17 km/h

Thu., 28 Sep.
29°
28°

15%

2 h

21 km/h

Fri., 29 Sep.
29°
29°

15%

6 h

28 km/h

Sat., 30 Sep.
29°
29°

15%

5 h

35 km/h

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.

Information about vacation rentals in Islamorada

🏡 Vacation rentals available 1,733 homes
💳 Possible discounts up to 44%
🌙 Nightly prices starting at $136
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 412 homes
🏊 Vacation rentals with pools 1,471 homes

Frequently Asked Questions

What is the typical price of a vacation home in Islamorada?

Accommodation prices in Islamorada start at $136 per night.

What is the typical availability of House rental in Islamorada?

We found 1,733 vacation homes in Islamorada available for your next trip.

What are the most popular vacation home amenities in Islamorada?

The most popular amenities for rentals in Islamorada include vacation homes with Pool, Internet, or Pets allowed.

How many House rental and Apartment rental can I find in Islamorada?

Islamorada has 1,733 House rental and Apartment rental available to book.

Are there pet-friendly vacation rentals in Islamorada?

Finding a vacation rental in Islamorada that allows dogs is definitely possible, with 412 pet-friendly homes on offfer.

What's the best month to visit Islamorada?

If you're looking for balmy weather, July and August are typically the hottest months in Islamorada with temperatures around 33 °C. February and January in Islamorada are the coldest, with 20 °C on average.

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