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Islamorada Vacation Rentals

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Choose from 1,793 vacation rentals and homes for your trip!

Best-rated vacation rentals in Islamorada

Discover vacation rentals with top-notch guest ratings

House Islamorada
from $1,973 per night
House ∙ 14 guests ∙ 6 bedrooms

House with barbeque, patio & private pool | Nature view | Perfect for remote work

5.0
Outstanding(73 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $544 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, barbeque & heated pool | Nature view | Perfect for remote work

5.0
Outstanding(57 ratings)
Islamorada, Monroe County, Florida, United States
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Villa Islamorada
from $124 per night
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with barbeque, garden & heated pool | Nature view | Suitable for remote work

4.7
Excellent(28 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

Condo Islamorada
from $763 per night
Condo ∙ 12 guests ∙ 5 bedrooms

Condo with grill | Water view | Suitable for remote work

5.0
Outstanding(3 ratings)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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House Islamorada
from $583 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio, garden & barbeque | Nature view | Good for workation

4.0
Very good(1 rating)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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House Islamorada
from $241 per night
House ∙ 12 guests ∙ 3 bedrooms

Vacation home with barbeque, garden & patio

4.7
Excellent(6 ratings)
Islamorada, Monroe County, Florida, United States
Pet-friendly
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See all pet-friendly offers

Vacation rentals with pool in Islamorada

Discover best cabin and house rentals with pool in Islamorada

Condo Islamorada
from $131 per night
Condo ∙ 3 guests ∙ 1 bedroom

Family-friendly condo with hot tub, barbeque & heated pool | Water view

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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House Islamorada
from $240 per night
House ∙ 10 guests ∙ 4 bedrooms

House with pool & terrace

Islamorada, Monroe County, Florida, United States
Pool
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House Islamorada
from $553 per night
House ∙ 8 guests ∙ 3 bedrooms

House with pool

3.0
(2 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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Best vacation rental offers in Islamorada

House Islamorada
from $271 per night
House ∙ 5 guests ∙ 1 bedroom

House with terrace & barbeque | Perfect for remote work

Islamorada, Monroe County, Florida, United States
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House Islamorada
from $163 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with garden, patio & heated pool | Nature view | Suitable for remote work

5.0
Outstanding(20 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $280 per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with terrace, grill & pool

5.0
Outstanding(40 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $967 per night
House ∙ 12 guests ∙ 4 bedrooms

Family-oriented pleasant house with grill | Water view | Beach nearby | Dogs allowed

4.7
Excellent(3 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $418 per night
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque, patio & heated pool

4.4
Very good(21 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $109 per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with pool, jacuzzi & barbeque

5.0
Outstanding(23 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $1,149 per night
House ∙ 14 guests ∙ 6 bedrooms

Vacation home with jacuzzi, barbeque & yard | Nature view

4.9
Outstanding(90 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $365 per night
House ∙ 12 guests ∙ 4 bedrooms

House with terrace, private pool & yard

5.0
Outstanding(10 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $387 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with 2 bedrooms for 6 persons

5.0
Outstanding(41 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $626 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with garden, private pool & patio | Perfect for remote work

5.0
Outstanding(10 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $158 per night
House ∙ 8 guests ∙ 3 bedrooms

Child-friendly beautiful house with private pool, yard & barbecue | Nature view | Suitable for remote work | Dogs allowed

5.0
Outstanding(9 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $726 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with private pool & barbecue

Islamorada, Monroe County, Florida, United States
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Condo Islamorada
from $208 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with patio, heated pool & barbeque

4.9
Outstanding(56 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $605 per night
House ∙ 8 guests ∙ 4 bedrooms

House with grill

3.9
Good(14 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $413 per night
House ∙ 12 guests ∙ 5 bedrooms

Child-friendly wonderful house with BBQ & terrace | Close to the beach | Perfect for remote work | Dogs allowed

5.0
Outstanding(30 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $177 per night
House ∙ 9 guests ∙ 2 bedrooms

Family-oriented nice vacation home with garden, BBQ & patio | Nature view

4.5
Excellent(7 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $393 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with barbeque & patio | Perfect for remote work

Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $723 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly house with private pool, terrace & grill | Pets allowed

5.0
Outstanding(31 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $935 per night
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly big vacation home with patio, grill & yard | Nature view | Pets allowed

4.8
Outstanding(80 ratings)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $231 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with patio

5.0
Outstanding(4 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $326 per night
House ∙ 12 guests ∙ 4 bedrooms

Fully equipped pleasant vacation home with jacuzzi, private pool & barbecue | Pet-friendly

4.8
Outstanding(19 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $295 per night
House ∙ 8 guests ∙ 2 bedrooms

House with barbeque, private pool & patio

5.0
Outstanding(82 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $433 per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, barbeque & hot tub

3.0
(1 rating)
Islamorada, Monroe County, Florida, United States
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House Islamorada
from $361 per night
House ∙ 3 guests ∙ 1 bedroom

Family-friendly house with barbeque | Beach view | Pets are welcome

5.0
Outstanding(4 ratings)
Islamorada, Monroe County, Florida, United States
View deal
Apartment Islamorada
from $217 per night
Apartment ∙ 10 guests ∙ 3 bedrooms

Children-friendly lovely rental apartment with private pool, terrace & garden

4.9
Outstanding(34 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $394 per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly pleasant vacation home with BBQ, terrace & jacuzzi

5.0
Outstanding(6 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $192 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden, BBQ & heated pool | Good for workation

4.6
Excellent(21 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $186 per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, heated pool & barbeque

5.0
Outstanding(8 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $825 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with garden, patio & private pool | Nature view | Good for workation | Dogs allowed

4.8
Outstanding(104 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Islamorada
from $240 per night
House ∙ 4 guests ∙ 2 bedrooms

House with yard, patio & barbeque | Nature view

5.0
Outstanding(14 ratings)
Islamorada, Monroe County, Florida, United States
View deal
Show all 1858 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 9/19 – 9/26 are the most affordable in the year, with vacation rental prices at $718 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 May (5/29 – 6/5). It's easiest to find a vacation rental in Islamorada in August - 81% of the holiday rentals in the area are still available.

And we love our apartments

House with terrace & barbeque | Perfect for remote work
Vacation home with garden, patio & heated pool | Nature view | Suitable for remote work
Fully equipped house with terrace, grill & pool
Family-oriented pleasant house with grill | Water view | Beach nearby | Dogs allowed
House with barbeque, patio & heated pool
Show all 1858 apartments in Islamorada

Features of Islamorada vacation rentals

💳 Discounts up to 73%
⭐ Popular amenities Pets allowed, Pool and Internet
🏊  Vacation rentals with a pool 1,455 rentals
🌙 Minimum price starting at $126
🐾 Pet friendly vacation homes 762 rentals
🏡 Rentals available 1,793 rentals

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