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Search results; Over 1,000 homes in Islamorada

This beachfront Islamorada condo puts you on a 180-foot pier over the bay
2 bedrooms, 4 beds, 2 private baths
Aug 22 – 27
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4.72 out of 5 average rating, 148 reviews
Superhost
This oceanfront Islamorada villa gives you a private beach, heated pool, and dock
New place to stay, 4 bedrooms, 4 beds, 4 baths
Aug 17 – 22
Top guest favorite
This solar-powered Islamorada houseboat gives you 360-degree views half a mile offshore
4.93 out of 5 average rating, 389 reviews, 1 bedroom, 1 bed, 1 bath
Aug 17 – 22
This solar-powered Islamorada houseboat puts you in a protected basin among islands
5.0 out of 5 average rating, 3 reviews, 2 beds, 1 bath
Aug 24 – 29
Top guest favorite
This Islamorada house puts you above a brewery with two balconies and a backyard garden
4.97 out of 5 average rating, 218 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 15 – 22
Top guest favorite
Watch the sunset from your private dock at this waterfront Islamorada house
5.0 out of 5 average rating, 54 reviews, 4 bedrooms, 4 beds, 3 baths
Sep 15 – 22
Sip your morning coffee on the deck of this Islamorada houseboat
4.83 out of 5 average rating, 118 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 22 – 27
Superhost
This waterfront Islamorada condo gives you a 30 ft boat slip and shared pool
New place to stay, 3 bedrooms, 4 beds, 2.5 baths
Aug 13 – 20
Top guest favorite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 12 – 18
Top guest favorite
This waterfront Florida Keys house gives you a private pool, boat slip, and fire pit
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 12 – 17
Guest favorite
This renovated oceanfront Islamorada house gives you a pool, boat slip, and kayaks
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 2.5 baths
Aug 22 – 29
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
4.91 out of 5 average rating, 34 reviews, 1 bedroom, 1 bed, 1 bath
Aug 13 – 18
This waterfront Islamorada house gives you canal access, a pool, and Snake Creek views
4 bedrooms, 5 beds, 3 baths
Jan 30 – Feb 4
Guest favorite
This Islamorada villa puts you bayside with a heated pool, dock, and tiki hut
4.95 out of 5 average rating, 21 reviews, 3 bedrooms, 3 beds, 3.5 baths
Aug 23 – 30
Top guest favorite
This Islamorada townhouse gives you ocean access, a dock, and a game room
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 3 baths
Aug 12 – 18
Top guest favorite
This canal-front Key Largo house gives you a private dock, hot tub, and kayak
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 1 bed, 3 baths
Aug 23 – 28
Guest favorite
Wake to sunrises on your triple-level Islamorada houseboat’s rooftop deck
4.9 out of 5 average rating, 274 reviews, 1 bedroom, 2 beds, 1 bath
Aug 24 – 29
Superhost
Water views greet you from the screened balcony of this Islamorada condo
New place to stay, 2 bedrooms, 3 beds, 2.5 baths
Aug 21 – 28
This poolside Islamorada apartment gives you beach access and a BBQ area
4.8 out of 5 average rating, 51 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21