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Vacation Rentals in Islamorada

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Islamorada
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Apartment
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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

House Islamorada
Sep 9 - Sep 16
-50%
$900
$450 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Islamorada with Ocean Pool + Pool Views
5.0
"Excellent" (88 ratings)
Islamorada, Monroe County, Florida, United States
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Villa Islamorada
Sep 16 - Sep 23
-15%
$277
$235 per night
Villa ∙ 4 guests ∙ 2 bedrooms
Pleasant Villa in Islamorada with Yard & Grill + Next to Beach
4.9
"Excellent" (36 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Nov 5 - Nov 12
-16%
$365
$307 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Islamorada with Pool, Yard & Grill + Degree Views
5.0
"Excellent" (94 ratings)
Islamorada, Monroe County, Florida, United States
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Discover a vacation home meeting your expectations among the 1,653 welcoming options from 8 providers in Islamorada. Using HomeToGo you can instantly search and compare the prices of each available property to discover the best deal and save up to 46%.

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Top-Rated Rentals and Accommodations in Islamorada

Cottage Islamorada
Nov 5 - Nov 12
$225 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Islamorada with Grill + Ocean Views
5.0
"Excellent" (116 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jul 29 - Aug 5
-42%
$450
$260 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Islamorada with Grill & Yard + Great Views
4.6
"Outstanding" (67 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Nov 5 - Nov 12
$315 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Large Pool + Ocean View
4.9
"Excellent" (55 ratings)
Islamorada, Monroe County, Florida, United States
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Recommended Vacation Rentals in Islamorada

Find your perfect vacation rental in Islamorada: from $130 per night

Cottage Islamorada
Dec 2 - Dec 9
$225 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Islamorada with Grill + Ocean Views
5.0
"Excellent" (116 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Dec 2 - Dec 9
$315 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Large Pool + Ocean View
4.9
"Excellent" (55 ratings)
Islamorada, Monroe County, Florida, United States
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Cottage Islamorada
Jul 29 - Aug 5
$275 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Lovely Cottage in Islamorada with Grill & Yard + Next to Beach
5.0
"Excellent" (79 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Sep 18 - Sep 25
-35%
$399
$257 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Nice Condo in Islamorada with Yard, Pool & Grill + Ocean View
5.0
"Excellent" (137 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Oct 15 - Oct 22
-49%
$343
$175 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Pool & Patio
4.8
"Excellent" (179 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Sep 9 - Sep 16
-20%
$199
$159 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Islamorada with Grill, Pool & Yard
4.9
"Excellent" (35 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Sep 9 - Sep 16
-60%
$395
$159 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Islamorada with Beautiful Pool
5.0
"Excellent" (12 ratings)
Islamorada, Monroe County, Florida, United States
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Villa Islamorada
May 3 - May 10
$229 per night
Villa ∙ 4 guests ∙ 1 bedroom
Villa in Islamorada with Yard & Grill
4.9
"Excellent" (108 ratings)
Islamorada, Monroe County, Florida, United States
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Cottage Islamorada
Sep 30 - Oct 7
$269 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Islamorada with Pool
4.8
"Excellent" (55 ratings)
Islamorada, Monroe County, Florida, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Islamorada

Condo Islamorada
Aug 19 - Aug 26
-27%
$300
$220 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Rental Condo in Islamorada with Outdoor Pool + Water Views
4.8
"Excellent" (141 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Sep 14 - Sep 21
-46%
$592
$319 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Electric Fireplace + Ocean Views
5.0
"Excellent" (151 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Dec 9 - Dec 16
$130 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Islamorada with Sauna, Pool & Grill + Ocean View
4.9
"Excellent" (72 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
Apr 20 - Apr 27
$130 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Islamorada with Sauna, Pool & Grill + Ocean View
4.9
"Excellent" (72 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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House Air conditioning Islamorada
Jul 29 - Aug 5
-42%
$451
$260 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Islamorada with Grill & Yard + Great Views
4.6
"Outstanding" (67 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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Condo Air conditioning Islamorada
Sep 30 - Oct 7
-34%
$301
$198 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Rental Condo in Islamorada with Outdoor Pool + Water Views
4.8
"Excellent" (141 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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Vacation rentals with Wi-Fi

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

Condo Internet Islamorada
Dec 2 - Dec 9
-24%
$334
$255 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
Internet
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Villa Internet Islamorada
Aug 19 - Aug 26
$236 per night
Villa ∙ 4 guests ∙ 2 bedrooms
Pleasant Villa in Islamorada with Yard & Grill + Next to Beach
4.9
"Excellent" (36 ratings)
Islamorada, Monroe County, Florida, United States
Internet
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House Internet Islamorada
Sep 12 - Sep 19
-47%
$599
$319 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Electric Fireplace + Ocean Views
5.0
"Excellent" (151 ratings)
Islamorada, Monroe County, Florida, United States
Internet
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Islamorada rental with full kitchen.

Condo Kitchen Islamorada
Dec 2 - Dec 9
$316 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Pleasant Condo in Islamorada with Large Pool + Ocean View
4.9
"Excellent" (55 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
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House Kitchen Islamorada
Sep 12 - Sep 19
$746 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Islamorada with Grill & Yard + Courtyard View
5.0
"Excellent" (4 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
Details
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House Kitchen Islamorada
Sep 9 - Sep 16
-24%
$233
$176 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Islamorada with Pool & Grill + Sunset View
4.6
"Outstanding" (31 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
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Popular Rental Amenities in Islamorada

  • Pool (1,433)
  • Pets allowed (346)
  • Fishing (1,051)
  • Air conditioning (1,505)
  • Balcony/Patio (546)
  • Kitchen (1,228)
  • Internet (1,622)
  • TV (1,504)
  • Washer (819)
  • Parking (36)
  • Grill (904)
  • Microwave (1,328)

Check above for the most selected filters in Islamorada and the number of vacation rentals that offer them. Many properties in Islamorada offer "Pool" or "Pets allowed," which makes it a wonderful vacation destination if you're dreaming of days spent poolside or you travel with your pet. You could even look for rentals if you want a rental with a fireplace (236 rentals include "Fireplace" in Islamorada) or if you want a rental providing a crib (106 rentals in Islamorada include "Crib").

Price and Availability Index in Islamorada

Vacation Rental Price Information in Islamorada

We analyzed vacation houses, cottages and apartments to display a price graph showing the average price per night in Islamorada. Prices rise in February and reach an average of $944 a night (2/17 - 2/24), making it the most expensive time to book a rental in the next 12 months. However, in October (10/28 - 11/4), prices decrease to an average of $492 per night.

Rental Availability Information in Islamorada

Check out the graph above to find out how many accommodations are available in Islamorada(in %). It is harder to find an accommodation during a week of May (5/4 - 5/11), as 66% of the rentals are booked. Conversely, you will find the highest percentage of available offers in Islamorada in November (11/25 - 12/2).

The Weather in Islamorada

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70°
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6 days 6
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81°
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16 days 16
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81°
72°
9 days 9
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79°
70°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Islamorada climate diagram. On average, the warmest month is July. On the contrary, the coolest month is February. The rainiest month is September while the driest month is February.

7-Day Weather Forecast in Islamorada

Sat, 3 Jun
80°
77°

5%

5 h

5 mi/h

Sun, 4 Jun
80°
78°

20%

6 h

5 mi/h

Mon, 5 Jun
82°
78°

15%

12 h

5 mi/h

Tue, 6 Jun
82°
78°

10%

12 h

4 mi/h

Wed, 7 Jun
82°
80°

15%

5 h

7 mi/h

Thu, 8 Jun
82°
80°

15%

4 h

13 mi/h

Fri, 9 Jun
82°
82°

15%

9 h

10 mi/h

Accommodations for your vacation in Islamorada

In Islamorada, many of the 1,653 vacation properties are house rental, which represent 66.67% of its listed properties. Additionally, the average nightly price of house rental there is $833, and the median size is 142 m². Furthermore, these accommodations are perfect for large groups, as most can accommodate 7 guests. If you would prefer to compare another accommodation type, you may want to check villa, which are the second most frequent accommodation type in Islamorada. The average size of villa in Islamorada is 233 m², and the average price is $1,462 per night.
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 1,653 properties
💳 Possible discounts up to 46%
🌙 Nightly prices starting at $130
⭐ Popular amenities Pool, Pets allowed and Fishing
🐾 Pet friendly accommodations 340 properties
🏊 Vacation rentals with pools 1,414 properties

Frequently Asked Questions

What is the nightly price for a vacation home in Islamorada?

The average accommodation in Islamorada is priced at $130 per night. If you’re interested in a house rental, the average price is $833 per night. A villa Islamorada will cost $1,462 per night on average.

How many vacation homes are available for booking in Islamorada?

There are 1,653 rentals to choose from for your next trip.

What amenities are most popular for vacation homes in Islamorada?

If you're looking to book a vacation rental in Islamorada, others search for homes with Pool, Pets allowed and Fishing.

How many vacation homes with pools are there in Islamorada?

There are 1,414 vacation homes across 8 providers in Islamorada.

Are dogs allowed in vacation homes in Islamorada?

Absolutely, there are 340 rentals in Islamorada that allow dogs and the average nightly rate is $953.

When is it better to travel to Islamorada?

July and August are the warmest months in Islamorada with temperatures around 91 °F. The coldest months in Islamorada are February and January, with 68 °F on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Islamorada TripAdvisor Vacation Rentals in Islamorada Vrbo Vacation Rentals in Islamorada VacationRentals.com Vacation Rentals in Islamorada HouseTrip Vacation Rentals in Islamorada FlipKey Vacation Rentals in Islamorada Homestay.com Vacation Rentals in Islamorada Only-apartments Vacation Rentals in Islamorada Interhome Vacation Rentals in Islamorada Novasol Vacation Rentals in Islamorada HomeEscape Vacation Rentals in Islamorada

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