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Search results; Over 1,000 homes in Islamorada

Top guest favorite
This solar-powered Islamorada houseboat gives you 360-degree views half a mile offshore
1 bedroom, 1 bed, 1 private bath
Aug 17 – 22
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4.93 out of 5 average rating, 389 reviews
Superhost
This Islamorada villa gives you a private beach, heated pool, and dock
New place to stay, 4 bedrooms, 4 beds, 4 baths
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
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 13 – 19
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
Top guest favorite
This Marathon waterfront house gives you a heated pool, dock, and sailing kayaks
5.0 out of 5 average rating, 87 reviews, 4 bedrooms, 8 beds, 3 baths
Oct 24 – 31
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 14 – 19
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
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
A 70ft dock and canal access await you at this Marathon house near the beach
4.94 out of 5 average rating, 203 reviews, 3 bedrooms, 5 beds, 3 baths
Aug 23 – 30
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
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
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 13 – 18
Superhost
Ocean views greet you from the private beach and infinity pool at this Islamorada house
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 4.5 baths
Aug 17 – 22
Top guest favorite
This Florida Keys house gives you a private pool, fire pit, and outdoor kitchen
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
Top guest favorite
This canal-front Islamorada home gives you a private pool and boat slip
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 13 – 18