filters

Search results; Over 1,000 homes in Islamorada

Guest favorite
This beachfront Islamorada house puts you on the water with kayaks and a shared pool
2 bedrooms, 4 beds, 2.5 private baths
Aug 15 – 22
,
4.86 out of 5 average rating, 63 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
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
Guest favorite
This Marathon houseboat anchors you among mangroves with a kayak and grill
4.92 out of 5 average rating, 90 reviews, 1 bedroom, 1 bed, 1 bath
Sep 27 – Oct 2
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
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
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
A historic courthouse turned waterfront home — you get a tiki bar and private dock in Islamorada
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 13 – 20
This renovated Tavernier condo gives you mangrove views from a private balcony
New place to stay, 2 bedrooms, 4 beds, 2 baths
Aug 17 – 22
Top guest favorite
This two-story 63 ft River Queen in Tavernier gives you 360-degree views
4.92 out of 5 average rating, 401 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 12 – 17
Top guest favorite
This elevated Islamorada apartment puts you steps from a boat basin and fishing jetty
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 24 – 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
Top guest favorite
Ocean views and a heated pool greet you at this Islamorada house with beach access
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 2.5 baths
Aug 29 – Sep 5
Top guest favorite
This waterfront Islamorada house gives you free dockage, a heated pool, and a game room
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 5 beds, 3 baths
Sep 17 – 24
Top guest favorite
Soak in the sun at this Key Largo cottage with a heated pool, kayaks, and marina
5.0 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 8 – 13
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
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