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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
,
4.93 out of 5 average rating, 393 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
12–19 Sept
4.97 out of 5 average rating, 219 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
18–25 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
10–16 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
10–17 Sept
New place to stay
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
20–26 Sept
4.97 out of 5 average rating, 35 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
12–17 Sept
4.77 out of 5 average rating, 52 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
13–18 Sept
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in Tavernier
Turtle Nest 1 Private beach,Pool, 2bed 2bath
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
4.91 out of 5 average rating, 143 reviews
Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Islamorada
The Nest Villa & Marina in the heart of Islamorada
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 18 reviews
Guest favourite
Cottage in Key Largo
Kampground Paradise w/Kayaks, Heated Pool & Marina
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 78 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 beds & pool
2 bedrooms, 2 beds, 1 bathroom
10–15 Sept
4.95 out of 5 average rating, 105 reviews
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
11–18 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds, 4 bathrooms
30 Oct – 4 Nov
4.87 out of 5 average rating, 47 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
22–29 Sept
New place to stay