Holiday lettings & accommodation in Islamorada - HolidayHomes base64Hash Holiday lettings & accommodation in Islamorada - HolidayHomes

Holiday lettings & accommodation in Islamorada

Find 1,754 available offers from 15 partners

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Top-Rated Lettings and Properties in Islamorada

Book Holiday Letting Offers with the Highest User Rating

House Islamorada
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
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House Islamorada
Next available - August 2026 - Oceanfront - Heated Pool - Dock
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House Islamorada
Private Beachfront Paradise
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House Islamorada
House with barbeque, private pool & terrace
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House Islamorada
Children-friendly big holiday home with garden, terrace & barbecue | Nature view | Pets allowed
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House Islamorada
Private Expansive Oceanfront 5 Bedroom Estate, Private Pier and Saltwater Pool
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House Islamorada
Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool
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House Islamorada
Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach
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House Islamorada
The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
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Apartment Islamorada
Children-friendly lovely apartment with private pool, terrace & garden
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House Islamorada
Waterfront home in the heart of the fishing capital of the world.
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House Islamorada
"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
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House Islamorada
3200sqft Masterpiece Home, Fishing Paradise, Waterfront, Beach, Pool, Islamorada
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Condo Islamorada
Ocean View with protected dock on lagoon with private boat ramp
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Villa Islamorada
Villa with barbeque, garden & heated pool | Nature view | Suitable for remote work
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Top 15 Recommended holiday lettings in Islamorada

Find your perfect vacation rental in Islamorada from just £76 per night!

House Islamorada
House ∙ 8 guests ∙ 2 bedrooms

Fully equipped charming house with pool & barbeque

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 8 guests and features a private pool for relaxation and enjoyment.
from £253
per night
View deal
House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with barbeque

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 8 guests and features a private balcony for stunning views.
from £455
per night
(14)
View deal
House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, garden & barbeque | Nature view | Good for workation

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 8 guests and features a lovely garden for relaxation.
from £437
per night
(1)
View deal
House Islamorada
House ∙ 10 guests ∙ 5 bedrooms

House with barbeque & terrace | Perfect for remote work

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 10 guests and features a family-friendly atmosphere with waterside access.
from £300
per night
View deal
House Islamorada
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with barbeque

Islamorada, Monroe County, Florida, United States
This charming house rental in Islamorada accommodates 6 guests and features a fully equipped kitchen for a comfortable stay.
from £231
per night
View deal
House Islamorada
House ∙ 9 guests ∙ 4 bedrooms

Holiday home with pool, garden & terrace | Perfect for remote work

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 9 guests and features a private pool for relaxation and enjoyment.
from £322
per night
(27)
View deal
House Islamorada
House ∙ 6 guests ∙ 2 bedrooms

Beautiful holiday home with heated pool | Pets allowed

Islamorada, Monroe County, Florida, United States
This charming house rental in Islamorada accommodates 6 guests and features a heated pool for a relaxing stay.
from £195
per night
View deal
House Islamorada
House ∙ 9 guests ∙ 2 bedrooms

Family-oriented nice holiday home with garden, BBQ & terrace | Nature view

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 9 guests and features a beautiful garden for relaxation.
from £132
per night
(7)
View deal
House Islamorada
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped house with private pool, terrace & barbecue | Pets are welcome

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 10 guests and features a private pool for a relaxing stay.
from £448
per night
View deal

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