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Islamorada Vacation Rentals

Browse 1,801 available vacation homes and compared across 18 trusted partners

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Top-Rated Vacation rentals in Islamorada

Book the highest-rated Islamorada vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Islamorada
Private Beachfront Paradise
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House Islamorada
Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool
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Condo Islamorada
Bayside Condo with Beach, Pool, Marina & Dockage, Pickle ball and Tennis
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House Islamorada
The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
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House Islamorada
Fully equipped house with terrace, grill & pool
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House Islamorada
"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
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House Islamorada
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
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House Islamorada
House with private pool & barbecue
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Condo Islamorada
Ocean View with protected dock on lagoon with private boat ramp
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House Islamorada
Vacation home with pool, jacuzzi & barbeque
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House Islamorada
Fully equipped pleasant vacation home with jacuzzi, private pool & barbecue | Pet-friendly
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House Islamorada
Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
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House Islamorada
House with terrace, private pool & yard
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House Islamorada
House with terrace, heated pool & barbeque
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House Islamorada
Family-friendly beautiful vacation home with pool, barbeque & terrace | Nature view
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Top 15 most Recommended Vacation Rentals in Islamorada

Discover your ideal Islamorada vacation rental with real-time comparisons of 1,801 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Islamorada
8 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a spacious balcony for relaxing and enjoying the views.
from $630
per night
(14)
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House Islamorada
House ∙ 10 guests ∙ 5 bedrooms

264 m² House

Islamorada, Monroe County, Florida, United States
Spacious house rental in Islamorada for 10 guests featuring a family-friendly atmosphere and waterfront access.
from $406
per night
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House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

95 m² House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a spacious yard for outdoor relaxation.
from $570
per night
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House Islamorada
8 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a private pool for relaxation and enjoyment.
from $740
per night
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House Islamorada
House ∙ 9 guests ∙ 2 bedrooms

133 m² House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 9 guests and features a spacious yard perfect for outdoor activities.
from $171
per night
(7)
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House Islamorada
10 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
Spacious house rental in Islamorada accommodates 10 guests and features a private pool for a relaxing getaway.
from $864
per night
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House Islamorada
House ∙ 5 guests ∙ 1 bedroom

100 m² House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 5 guests and features a waterfront view with convenient parking.
from $265
per night
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House Islamorada
8 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a private pool for a relaxing getaway.
from $458
per night
(12)
View deal
House Islamorada
House ∙ 12 guests ∙ 6 bedrooms

242 m² House

Islamorada, Monroe County, Florida, United States
Spacious house rental in Islamorada for 12 with a private pool and family-friendly amenities.
from $570
per night
(31)
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