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Islamorada Vacation Rentals

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Choose from 1,902 vacation rentals and homes for your trip!

Best-rated vacation rentals in Islamorada

Discover vacation rentals with top-notch guest ratings

House Islamorada
from $1,377 per night
House ∙ 12 guests ∙ 5 bedrooms

372 m² House

5.0
Outstanding(76 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $208 per night
House ∙ 10 guests ∙ 3 bedrooms

372 m² House

5.0
Outstanding(33 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $516 per night
House ∙ 9 guests ∙ 4 bedrooms

130 m² House

4.9
Outstanding(26 ratings)
Islamorada, Monroe County, Florida, United States
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Pet-friendly rentals in Islamorada

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House Islamorada
from $417 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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House Islamorada
from $2,342 per night
14 guests ∙ 6 bedrooms

House

5.0
Outstanding(71 ratings)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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House Islamorada
from $376 per night
House ∙ 10 guests ∙ 4 bedrooms

267 m² House

4.4
Very good(3 ratings)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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Vacation rentals with pool in Islamorada

Discover best cabin and house rentals with pool in Islamorada

House Islamorada
from $641 per night
6 guests ∙ 3 bedrooms

House

4.4
Very good(25 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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House Islamorada
from $358 per night
6 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
Pool
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House Islamorada
from $805 per night
House ∙ 8 guests ∙ 4 bedrooms

314 m² House

5.0
Outstanding(50 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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Best vacation rental offers in Islamorada

House Islamorada
from $1,140 per night
House ∙ 14 guests ∙ 6 bedrooms

511 m² House

4.9
Outstanding(79 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $616 per night
House ∙ 8 guests ∙ 3 bedrooms

186 m² House

5.0
Outstanding(6 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $264 per night
House ∙ 4 guests ∙ 2 bedrooms

106 m² House

5.0
Outstanding(12 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $255 per night
House ∙ 6 guests ∙ 2 bedrooms

139 m² House

5.0
Outstanding(69 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $414 per night
16 guests ∙ 4 bedrooms

House

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $197 per night
House ∙ 9 guests ∙ 2 bedrooms

133 m² House

4.5
Excellent(7 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $1,111 per night
House ∙ 10 guests ∙ 4 bedrooms

465 m² House

5.0
Outstanding(83 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $186 per night
House ∙ 6 guests ∙ 3 bedrooms

127 m² House

4.7
Excellent(26 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $366 per night
House ∙ 8 guests ∙ 3 bedrooms

266 m² House

4.8
Outstanding(10 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $928 per night
House ∙ 8 guests ∙ 4 bedrooms

229 m² House

4.9
Outstanding(81 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $290 per night
6 guests ∙ 3 bedrooms

House

4.5
Excellent(8 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $1,012 per night
House ∙ 8 guests ∙ 4 bedrooms

223 m² House

4.8
Outstanding(29 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
from $279 per night
Condo ∙ 6 guests ∙ 2 bedrooms

110 m² Condo

4.9
Outstanding(109 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $1,106 per night
House ∙ 10 guests ∙ 5 bedrooms

316 m² House

5.0
Outstanding(25 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $663 per night
House ∙ 8 guests ∙ 3 bedrooms

279 m² House

4.8
Outstanding(66 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $211 per night
6 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
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House Islamorada
from $217 per night
House ∙ 6 guests ∙ 2 bedrooms

93 m² House

4.4
Very good(23 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $414 per night
House ∙ 10 guests ∙ 3 bedrooms

186 m² House

4.9
Outstanding(14 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $214 per night
6 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
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House Islamorada
from $409 per night
House ∙ 6 guests ∙ 3 bedrooms

130 m² House

4.9
Outstanding(97 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $641 per night
8 guests ∙ 4 bedrooms

House

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $510 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(12 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $358 per night
8 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
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House Islamorada
from $695 per night
House ∙ 8 guests ∙ 4 bedrooms

179 m² House

5.0
Outstanding(123 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $533 per night
House ∙ 12 guests ∙ 5 bedrooms

228 m² House

5.0
Outstanding(5 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
from $241 per night
6 guests ∙ 3 bedrooms

Condo

4.9
Outstanding(60 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $237 per night
8 guests ∙ 2 bedrooms

House

Islamorada, Monroe County, Florida, United States
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House Islamorada
from $2,468 per night
House ∙ 18 guests ∙ 9 bedrooms

683 m² House

Islamorada, Monroe County, Florida, United States
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House Islamorada
from $205 per night
House ∙ 6 guests ∙ 3 bedrooms

121 m² House

5.0
Outstanding(4 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $366 per night
House ∙ 8 guests ∙ 3 bedrooms

149 m² House

5.0
Outstanding(19 ratings)
Islamorada, Monroe County, Florida, United States
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Show all 1758 apartments in Islamorada

Price and Availability Index in Islamorada

Click on any bar to see price and availability information

Vacation Rental Price Information in Islamorada

Above, you can see a graph which shows changes in the price of vacation rentals in Islamorada. December is the priciest month to book a vacation rental, so make sure to book in advance for this period to get the best offer. In contrast, September and the period of 9/20 – 9/27 are the most affordable in the year, with vacation rental prices at $510 per night.

Rental availability information in Islamorada

This graph shows the availability rate in Islamorada over the next year. The busiest week of the year is in June (6/27 – 7/4). It's easiest to find a vacation rental in Islamorada in September - 75% of the holiday rentals in the area are still available.

5 reviews
5 travelers who stayed in Islamorada rated their vacation home 3.8/5 stars on average.

And we love our apartments

511 m² House
186 m² House
106 m² House
139 m² House
House
Show all 1758 apartments in Islamorada

Features of Islamorada vacation rentals

💳 Discounts up to 73%
⭐ Popular amenities Pets allowed, Pool and Internet
🏊  Vacation rentals with a pool 1,559 rentals
🌙 Minimum price starting at $167
🐾 Pet friendly vacation homes 734 rentals
🏡 Rentals available 1,902 rentals

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