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Islamorada Vacation Rentals

Browse 1,844 available vacation homes and compared across 19 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
Oceanfront 165ft Beach-Dock-Pool-4K sq. ft 4 bed-5 bath - Islamorada
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Condo Islamorada
October last Minute Special...Bayside Condo with Beach, Pool, Marina & Dockage
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House Islamorada
Islamorada Boaters Paradise with 70' Dock and private beach access..
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House Islamorada
Tropical Keys Retreat – Fully Furnished 3 Bed, 3 Bath Waterfront Gem. Sleeps 8
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House Islamorada
Blue Dolphin Oceanfront Estate, Millionaire's Row, Private Saltwater Pool
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House Islamorada
The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach
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House Islamorada
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
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House Islamorada
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
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House Islamorada
Vacation home with grill, jacuzzi & private pool | Nature view | Suitable for remote work
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House Islamorada
Vacation home with terrace & grill
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House Islamorada
Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi
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House Islamorada
Family-friendly charming house with terrace, hot tub & private pool | Perfect for remote work | Pets allowed
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House Islamorada
Sunset Peninsula—a multi-family, original, Florida Keys waterfront retreat!
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House Islamorada
Family-friendly beautiful vacation home with pool, barbeque & terrace | Nature view
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House Islamorada
House with patio, BBQ & private pool | Nature view | Good for workation
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Top 15 most Recommended Vacation Rentals in Islamorada

Discover your ideal Islamorada vacation rental with real-time comparisons of 1,844 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Islamorada
10 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
Spacious house rental in Islamorada for 10 guests featuring a private pool and a fully equipped kitchen for a perfect getaway.
from $678
per night
(2)
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House Islamorada
8 guests ∙ 3 bedrooms

House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a waterfront view with a private pool.
from $563
per night
(2)
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House Islamorada
8 guests ∙ 2 bedrooms

House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a pool for a relaxing stay.
from $246
per night
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Condo Islamorada
3 guests ∙ 1 bedroom

Condo

Islamorada, Monroe County, Florida, United States
This 3-bedroom condo in Islamorada features a balcony with stunning views and is perfect for a family getaway.
from $138
per night
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House Islamorada
House ∙ 10 guests ∙ 5 bedrooms

316 m² House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 10 guests and features a private pool perfect for a relaxing getaway.
from $1,095
per night
(27)
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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 $182
per night
(7)
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Condo Islamorada
Condo ∙ 6 guests ∙ 2 bedrooms

96 m² Condo

Islamorada, Monroe County, Florida, United States
This condo in Islamorada accommodates 6 guests and features a pool for relaxation and fun.
from $136
per night
(14)
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Villa Islamorada
Villa ∙ 6 guests ∙ 3 bedrooms

156 m² Villa

Islamorada, Monroe County, Florida, United States
This charming villa in Islamorada accommodates 6 guests and features a beautiful waterfront view with a private pool.
from $410
per night
(6)
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House Islamorada
House ∙ 4 guests ∙ 2 bedrooms

162 m² House

Islamorada, Monroe County, Florida, United States
Charming house rental in Islamorada accommodates 4 guests and features a waterfront view with a spacious balcony.
from $183
per night
(1)
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