Vacation Rentals in Islamorada - HomeToGo base64Hash Vacation Rentals in Islamorada - HomeToGo

Vacation Rentals in Islamorada

Find 1,958 available offers from 17 partners
Islamorada
Anytime
Guests
Islamorada
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Guests

Popular Filters to find the Perfect Home Rental in Islamorada

2 Adults
1 Bedroom
Pool
House
4 Adults
Pets allowed
2 Bedrooms

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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Vacation rentals and apartments with air conditioning

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

House  Islamorada
Feb 2 - Feb 9
$500 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Islamorada with Patio, Grill & Pool

Islamorada, Monroe County, Florida, United States
Free cancellation
Air conditioning
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House  Islamorada
Nov 9 - Nov 16
$598 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Islamorada with Grill

4.2
Very good (22 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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House  Islamorada
Oct 26 - Nov 2
-27%
$329
$239 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Islamorada

4.7
Excellent (21 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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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  Islamorada
Jul 6 - Jul 13
$500 per night
Condo ∙ 12 guests ∙ 5 bedrooms

Condo in Islamorada + Ocean Views

Islamorada, Monroe County, Florida, United States
Kitchen
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House  Islamorada
Sep 21 - Sep 28
$255 per night
House ∙ 2 guests ∙ 1 bedroom

Lovely House in Islamorada with Grill & Pool

5.0
Outstanding (29 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
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Condo  Islamorada
Sep 7 - Sep 14
$185 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Pleasant Condo in Islamorada with Pool & Patio

4.8
Outstanding (194 ratings)
Islamorada, Monroe County, Florida, United States
Kitchen
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Vacation rentals with Wi-Fi

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

House  Islamorada
Nov 9 - Nov 16
$1,822 per night
House ∙ 14 guests ∙ 6 bedrooms

Vacation Home in Islamorada with Yard & Pool + Gorgeous Views

5.0
Outstanding (59 ratings)
Islamorada, Monroe County, Florida, United States
Internet
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House  Islamorada
Nov 9 - Nov 16
$533 per night
House ∙ 10 guests ∙ 5 bedrooms

Beautiful Vacation Home in Islamorada with Spacious Terrace

Islamorada, Monroe County, Florida, United States
Internet
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House  Islamorada
Aug 17 - Aug 24
-65%
$1,715
$600 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Islamorada with Patio, Yard & Grill

4.8
Outstanding (27 ratings)
Islamorada, Monroe County, Florida, United States
Internet
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Best Vacation Home Deals in Islamorada

Save up to 36%

Condo Islamorada
Oct 26 - Nov 2
-36%
$250
$160 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Islamorada with Grill, Pool & Patio

4.9
Outstanding (57 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Nov 9 - Nov 16
-25%
$479
$359 per night
House ∙ 6 guests ∙ 3 bedrooms

Great Vacation Home in Islamorada with Grill + Water Views

4.7
Excellent (31 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Nov 9 - Nov 16
-20%
$448
$359 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Islamorada

3.9
Good (13 ratings)
Islamorada, Monroe County, Florida, United States
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Discover a vacation home meeting your expectations among the 1,958 welcoming options from 19 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 27%.

Recommended Vacation Rentals in Islamorada

Find your perfect vacation rental in Islamorada: from $157 per night

House Islamorada
Aug 31 - Sep 7
$1,000 per night
House ∙ 14 guests ∙ 5 bedrooms

House in Islamorada with Private Balcony

4.8
Outstanding (15 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jan 25 - Feb 1
$957 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Islamorada with Patio, Grill & Pool

4.6
Excellent (43 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Sep 7 - Sep 14
$230 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Islamorada with Large Balcony + Ocean Views

4.9
Outstanding (107 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Aug 31 - Sep 7
-26%
$1,357
$999 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Islamorada with Yard, Patio & Grill + Ocean Views

5.0
Outstanding (74 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jun 29 - Jul 6
-35%
$986
$643 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Islamorada with Private Terrace + Ocean Views

5.0
Outstanding (56 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Oct 26 - Nov 2
-25%
$399
$300 per night
House ∙ 5 guests ∙ 2 bedrooms

Pleasant Vacation Home in Islamorada with Yard, Pool & Grill

5.0
Outstanding (37 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Aug 31 - Sep 7
-39%
$1,295
$795 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Islamorada with Grill, Pool & Yard + Ocean Views

4.8
Outstanding (93 ratings)
Islamorada, Monroe County, Florida, United States
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Accommodation Islamorada
Nov 2 - Nov 9
$1,287 per night
Accommodation ∙ 18 guests ∙ 6 bedrooms

Rental in Islamorada with Grill, Patio & Yard

Islamorada, Monroe County, Florida, United States
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House Islamorada
Nov 9 - Nov 16
-18%
$1,867
$1,523 per night
House ∙ 10 guests ∙ 5 bedrooms

Wonderful Vacation Home in Islamorada with Pool & Grill + Spectacular Views

5.0
Outstanding (52 ratings)
Islamorada, Monroe County, Florida, United States
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Budget-friendly Vacation Rentals in Islamorada

Find Fantastic yet Inexpensive Offers

House Islamorada
Sep 7 - Sep 14
-56%
$225
$99 per night
House ∙ 4 guests ∙ 2 bedrooms

Beautiful Vacation Home in Islamorada with Pool & Patio

5.0
Outstanding (1 rating)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Dec 14 - Dec 21
-22%
$1,135
$881 per night
House ∙ 14 guests ∙ 5 bedrooms

Beautiful House in Islamorada with Private Pool + Beautiful Views

4.6
Excellent (18 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Aug 10 - Aug 17
$236 per night
House ∙ 3 guests ∙ 1 bedroom

House in Islamorada with Grill + Beautiful Views

5.0
Outstanding (1 rating)
Islamorada, Monroe County, Florida, United States
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Top-Rated Rentals and Accommodations in Islamorada

Book Vacation Rental Offers with the Highest User Rating

Condo Islamorada
Sep 7 - Sep 14
-25%
$175
$132 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo in Islamorada with Private Balcony

4.5
Excellent (124 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jul 6 - Jul 13
-30%
$500
$350 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Islamorada

5.0
Outstanding (23 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Nov 9 - Nov 16
-21%
$851
$672 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Islamorada with Pool & Grill + Beautiful Views

4.9
Outstanding (18 ratings)
Islamorada, Monroe County, Florida, United States
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Popular Rental Amenities in Islamorada

  • Pool (1,587)
  • Pet-friendly (480)
  • Fishing (1,318)
  • Air conditioning (1,893)
  • Balcony/patio (971)
  • Kitchen (1,464)
  • WiFi (1,857)
  • TV (1,752)
  • Washing machine (1,085)
  • Grill (1,167)
  • Microwave (1,456)
  • Dishwasher (979)

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 want a rental with a pool or you bring your pet everywhere. You could even look for rentals if you want a rental with a fireplace (255 rentals include "Fireplace" in Islamorada) or if you need a crib for your baby (222 rentals in Islamorada include "Crib").

Price and Availability Index in Islamorada

Click on any bar to see price and availability information

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 March and reach an average of $1,059 a night (3/22 – 3/29), making it the most expensive time to book a rental in the next 12 months. However, in September (9/28 – 10/5), prices decrease to an average of $451 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 (5/10 – 5/17), as 89% of the rentals are booked. Conversely, you will find the highest percentage of available offers in Islamorada in November (11/30 – 12/7).

The Weather in Islamorada

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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

Wed, 19 Jun
82°
80°

10%

2 h

19 mi/h

Thu, 20 Jun
82°
78°

40%

3 h

17 mi/h

Fri, 21 Jun
82°
82°

15%

2 h

17 mi/h

Sat, 22 Jun
82°
82°

15%

2 h

14 mi/h

Sun, 23 Jun
82°
82°

10%

5 h

13 mi/h

Mon, 24 Jun
84°
84°

10%

6 h

3 mi/h

Tue, 25 Jun
80°
80°

15%

2 h

17 mi/h

Accommodations for your vacation in Islamorada

In Islamorada, many of the 1,958 vacation properties are house rental, which represent 66.47% of its listed properties. Additionally, the average nightly price of house rental there is $813, and the median size is 162 m². Furthermore, these accommodations are perfect for large groups, as most can accommodate 8 guests. If you would prefer to compare another accommodation type, you may want to check condo, which are the second most frequent accommodation type in Islamorada. The average size of condo in Islamorada is 113 m², and the average price is $395 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 available 1,958 rentals
💳 Possible discounts up to 27%
🌙 Nightly prices starting at $157
⭐ Popular amenities Pool, Pets allowed and Fishing
🐾 Pet friendly homes 491 homes
🏊 Vacation rentals with pools 1,588 homes
7 reviews
Islamorada vacation rentals have an average rating of 4.2/5 on 7 reviews left by travelers.

Frequently Asked Questions

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

The average accommodation in Islamorada is priced at $157 per night. If you’re interested in a house rental, the average price is $813 per night. A condo Islamorada will cost $395 per night on average.

How many vacation homes are available for booking in Islamorada?

There are 1,958 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 1,588 vacation homes across 19 providers in Islamorada.

Are dogs allowed in vacation homes in Islamorada?

Absolutely, there are 491 rentals in Islamorada that allow dogs and the average nightly rate is $850.

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.

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