Islamorada Vacation Rentals - HolidayHomes base64Hash Islamorada Vacation Rentals - HolidayHomes

Islamorada Vacation Rentals

Browse 1,718 available vacation homes and compared across 14 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
Now booking heavily for 2027! - Oceanfront - Heated Pool - Dock
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House Islamorada
New saltwater pool, pet friendly, waterfront house with dock
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House Islamorada
Best Location in Islamorada! Beach access - Boat trailer parking!
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House Islamorada
Vacation home with patio
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Villa Islamorada
Fully equipped villa with private pool, terrace & grill | City view | Next to the beach
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House Islamorada
Morada Breeze 6 Bedroom Plantation Key Home with Pool & Dockage
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House Islamorada
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
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House Islamorada
Large 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
The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
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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 | Suitable for remote work
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House Islamorada
House with yard, patio & barbeque | Nature view
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House Islamorada
Islamorada, Indian Waterways, waterfront retreat - heated pool, 30’ dock
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House Islamorada
Charming 3BR canal home in Islamorada, perfect for your tropical getaway!
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Top 15 most Recommended Vacation Rentals in Islamorada

Discover your ideal Islamorada vacation rental with real-time comparisons of 1,718 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Accommodation Islamorada
Accommodation ∙ 18 guests ∙ 6 bedrooms

Rental with terrace, BBQ & garden | Water view

Islamorada, Monroe County, Florida, United States
This spacious accommodation in Islamorada accommodates 18 guests and features waterfront access for a perfect getaway.
from $1,944
per night
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House Islamorada
House ∙ 4 guests ∙ 2 bedrooms

Children-friendly vacation home with barbeque | Water view | Close to the beach | Good for workation | Pets are welcome

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 4 guests and features a beautiful sea view.
from $231
per night
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House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

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

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a spacious yard for outdoor relaxation.
from $579
per night
(2)
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House Islamorada
House ∙ 10 guests ∙ 4 bedrooms

House with pool & terrace

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 10 guests and features a beautiful waterfront view with a private pool.
from $258
per night
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House Islamorada
House ∙ 9 guests ∙ 2 bedrooms

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

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 9 guests and features a spacious yard perfect for outdoor activities.
from $182
per night
(7)
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House Islamorada
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped charming vacation home with patio & grill | Nature view | Pet-friendly

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a waterfront view with ample parking available.
from $287
per night
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House Islamorada
House ∙ 8 guests ∙ 2 bedrooms

House with barbeque, private pool & patio

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 6 guests and features a private pool for relaxation and enjoyment.
from $321
per night
(82)
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Condo Islamorada
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with patio, heated pool & barbeque

Islamorada, Monroe County, Florida, United States
This spacious 6-person condo in Islamorada features a stunning waterfront view and a relaxing balcony for ultimate enjoyment.
from $207
per night
(60)
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House Islamorada
House ∙ 14 guests ∙ 3 bedrooms

House with barbeque, yard & pool

Islamorada, Monroe County, Florida, United States
Spacious house rental in Islamorada for 16 with a pool and ample parking, perfect for family gatherings or group retreats.
from $401
per night
(4)
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