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Islamorada Vacation Rentals

Anytime
1 guest
Anytime
1 guest
Choose from 2,455 vacation rentals and homes for your trip!

Best-rated vacation rentals in Islamorada

Discover vacation rentals with top-notch guest ratings

House Islamorada
from $1,715 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(54 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $765 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(52 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $324 per night
House ∙ 9 guests ∙ 4 bedrooms
4.9
Outstanding(14 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 $982 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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House Islamorada
from $994 per night
House ∙ 14 guests ∙ 6 bedrooms
4.6
Excellent(19 ratings)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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House Islamorada
from $1,015 per night
House ∙ 14 guests ∙ 6 bedrooms
4.9
Outstanding(73 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 $226 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding(14 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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Condo Islamorada
from $139 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.7
Excellent(6 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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House Islamorada
from $647 per night
House ∙ 6 guests ∙ 3 bedrooms
4.3
Very good(19 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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Best vacation rental offers in Islamorada

House Islamorada
from $192 per night
House ∙ 6 guests ∙ 3 bedrooms
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $304 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(4 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $597 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
from $119 per night
Condo ∙ 3 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
from $500 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(16 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $660 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(119 ratings)
Islamorada, Monroe County, Florida, United States
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Cottage Islamorada
from $173 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
4.7
Excellent(12 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $393 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(66 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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Condo Islamorada
from $223 per night
Condo ∙ 6 guests ∙ 4 bedrooms
4.9
Outstanding(58 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $935 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(41 ratings)
Islamorada, Monroe County, Florida, United States
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Accommodation Islamorada
from $1,957 per night
Accommodation ∙ 18 guests ∙ 6 bedrooms
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
from $224 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent(18 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $2,077 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(69 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $227 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(14 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $1,337 per night
House ∙ 12 guests ∙ 5 bedrooms
4.9
Outstanding(91 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $662 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(128 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $503 per night
House ∙ 14 guests ∙ 4 bedrooms
5.0
Outstanding(26 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $211 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(8 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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Villa Islamorada
from $463 per night
Villa ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(50 ratings)
Islamorada, Monroe County, Florida, United States
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Condo Islamorada
from $309 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(105 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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Condo Islamorada
from $218 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.0
Very good(1 rating)
Islamorada, Monroe County, Florida, United States
HomeToGo
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House Islamorada
from $1,485 per night
House ∙ 18 guests ∙ 6 bedrooms
5.0
Outstanding(8 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $873 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(20 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $308 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent(6 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $152 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $1,807 per night
House ∙ 14 guests ∙ 7 bedrooms
5.0
Outstanding(69 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $204 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $327 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent(22 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $239 per night
House ∙ 4 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
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Cottage Islamorada
from $183 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
Islamorada, Monroe County, Florida, United States
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Show all 2266 apartments in Islamorada

Price and Availability Index in Islamorada

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Vacation Rental Price Information in Islamorada

Above, you can see a graph which shows changes in the price of vacation rentals in Islamorada. November 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, January and the period of 1/3 – 1/10 are the most affordable in the year, with vacation rental prices at $505 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 November (11/15 – 11/22). It's easiest to find a vacation rental in Islamorada in June - 61% of the holiday rentals in the area are still available.

448,387 reviews
448,387 travelers who stayed in Islamorada rated their vacation home 4.5/5 stars on average.

And we love our apartments

92 m² House
House
390 m² House
57 m² Condo
195 m² Condo
Show all 2266 apartments in Islamorada

Features of Islamorada vacation rentals

💳 Discounts up to 73%
⭐ Popular amenities Pets allowed, Pool and Internet
🏊  Vacation rentals with a pool 1,764 rentals
🌙 Minimum price starting at $119
🐾 Pet friendly vacation homes 864 rentals
🏡 Rentals available 2,453 rentals

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