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Islamorada Vacation Rentals

Find 1,945 available offers from 17 partners
Islamorada
Anytime
Guests
Islamorada
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Guests

Popular Filters to find the Perfect Rental in Islamorada

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

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.

Show all 1,945 properties

Vacation rentals and apartments with air conditioning

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

House  Islamorada
Jun 29 - Jul 6
$595 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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Condo  Islamorada
Jun 29 - Jul 6
$290 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo in Islamorada with Private Balcony

4.5
Excellent (126 ratings)
Islamorada, Monroe County, Florida, United States
Air conditioning
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House  Islamorada
Jun 29 - Jul 6
$1,953 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Islamorada with Grill, Yard & Pool

4.9
Outstanding (79 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
Jun 15 - Jun 22
$1,204 per night
Condo ∙ 12 guests ∙ 5 bedrooms

Condo in Islamorada + Ocean Views

Islamorada, Monroe County, Florida, United States
Kitchen
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Condo  Islamorada
Sept 14 - Sept 21
-36%
$602
$383 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Superior Condo in Islamorada with Pool + Water Views

5.0
Outstanding (8 ratings)
Islamorada, Monroe County, Florida, United States
Free cancellation
Kitchen
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Condo  Islamorada
Nov 23 - Nov 30
-22%
$696
$542 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Pleasant Condo in Islamorada with Pool

5.0
Outstanding (4 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.

Condo  Islamorada
Nov 23 - Nov 30
-8%
$455
$421 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Rental Condo in Islamorada with Outdoor Pool + Spectacular Views

4.9
Outstanding (166 ratings)
Islamorada, Monroe County, Florida, United States
Internet
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House  Islamorada
Aug 10 - Aug 17
$536 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
Internet
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Condo  Islamorada
Jun 29 - Jul 6
$595 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Islamorada with Large Balcony + Spectacular Views

4.7
Excellent (86 ratings)
Islamorada, Monroe County, Florida, United States
Internet
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Best Vacation Home Deals in Islamorada

Save up to 7%

Condo Islamorada
Jun 22 - Jun 29
-7%
$450
$419 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Tavernier with Yard, Pool & Grill + Ocean Views

4.9
Outstanding (75 ratings)
Islamorada, Monroe County, Florida, United States
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1,945 beautiful vacation rentals from 17 vacation rental websites are listed in Islamorada, with prices beginning at $221 per night. HomeToGo instantly shows the best offers by comparing all of the listed vacation homes in Islamorada from its various partners.

Recommended Vacation Rentals in Islamorada

Find your perfect vacation rental in Islamorada: from $221 per night

Condo Islamorada
Jun 29 - Jul 6
$413 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Charming Condo in Islamorada with Private Balcony

4.7
Excellent (69 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Jun 29 - Jul 6
$493 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Islamorada with Large Pool

4.7
Excellent (113 ratings)
Islamorada, Monroe County, Florida, United States
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Accommodation Islamorada
Nov 2 - Nov 9
$2,872 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
Jun 29 - Jul 6
$1,019 per night
House ∙ 8 guests ∙ 4 bedrooms

Lovely House in Islamorada with Patio, Pool & Grill

4.9
Outstanding (80 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
Jun 21 - Jun 28
$288 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo in Islamorada with Sauna, Pool & Grill + Ocean View

5.0
Outstanding (146 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Feb 2 - Feb 9
$730 per night
House ∙ 6 guests ∙ 2 bedrooms

House in Islamorada with Patio, Grill & Pool

Islamorada, Monroe County, Florida, United States
Free cancellation
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Villa Islamorada
Jun 29 - Jul 6
$602 per night
Villa ∙ 6 guests ∙ 2 bedrooms

Beautiful Villa in Islamorada with Patio, Yard & Pool

5.0
Outstanding (117 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jun 29 - Jul 6
$1,223 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Islamorada with Large Pool

5.0
Outstanding (32 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jun 15 - Jun 22
$1,489 per night
House ∙ 12 guests ∙ 4 bedrooms

Pleasant House in Islamorada with Grill + Water Views

Islamorada, Monroe County, Florida, United States
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Budget-friendly Rentals in Islamorada

Find Fantastic yet Inexpensive Rentals

Apartment Islamorada
Jun 29 - Jul 6
$282 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment in Conch Key with Ample Parking

3.7
Good (12 ratings)
Islamorada, Monroe County, Florida, United States
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Boat Islamorada
Oct 5 - Oct 12
$513 per night
Boat ∙ 6 guests ∙ 3 bedrooms

Boat in Key Largo with Patio, Grill & Pool

4.9
Outstanding (300 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
Jun 29 - Jul 6
$919 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Layton with Patio, Grill & Pool + Fabulous Views

5.0
Outstanding (10 ratings)
Islamorada, Monroe County, Florida, United States
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Top-Rated Offers and Accommodations in Islamorada

Book Vacation Rentals with the Highest User Rating

House Islamorada
$2,439 per night
House ∙ 10 guests ∙ 5 bedrooms

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

5.0
Outstanding (53 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
$481 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home in Islamorada with Pool, Yard & Patio

4.9
Outstanding (22 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
$455 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Islamorada with Pool

5.0
Outstanding (2 ratings)
Islamorada, Monroe County, Florida, United States
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Popular Rental Amenities in Islamorada

  • Pool (1,582)
  • WiFi (1,854)
  • Pet-friendly (487)
  • Air conditioning (1,891)
  • Kitchen (1,462)
  • Balcony/patio (978)
  • Washing machine (1,076)
  • TV (1,748)
  • Fishing (1,316)
  • Dishwasher (981)
  • Grill (1,163)
  • Microwave (1,447)

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 7 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 many 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 (2/15 – 2/22). During this week, a night will cost on average $1,582. The week with the lowest average prices is in October (10/26 – 11/2).

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 May (5/10 – 5/17). Conversely, it is in September (9/28 – 10/5) that the highest percentage of vacation homes are available.

The Weather in Islamorada

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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. No heat wave is expected in February, where minimum average temperatures usally hit a 20° low. September is the wettest month.

7-Day Weather Forecast in Islamorada

Fri., 14 Jun.
28°
27°

25%

1 h

13 km/h

Sat., 15 Jun.
28°
27°

10%

0 h

15 km/h

Sun., 16 Jun.
28°
28°

10%

0 h

9 km/h

Mon., 17 Jun.
28°
28°

15%

2 h

21 km/h

Tue., 18 Jun.
28°
28°

15%

4 h

23 km/h

Wed., 19 Jun.
28°
28°

15%

1 h

27 km/h

Thu., 20 Jun.
28°
28°

15%

0 h

26 km/h

Accommodations for your vacation in Islamorada

Users who are searching for house rental in Islamorada can find many alternatives, as they are the most prevalent accomodations being offered there. Interestingly, specific accommodation type, this specific accommodation type is $1,130 per night, with an average size of 160 m². Furthermore, these vacation homes are ideal for large groups, as most can accommodate 8 guests. Condo are the other most typical property type in Islamorada. Condo in Islamorada are 114 m² on average, with prices averaging $550 a 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 1,945 rentals
🌙 Nightly prices starting at $221
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 490 homes
🏊 Vacation rentals with pools 1,582 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 typical availability of vacation rentals in Islamorada?

At the moment, there are 1,945 vacation homes from 17 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 25% 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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