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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
2 bedrooms, 3 beds, 1 private bathroom
14–19 Sept
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4.82 out of 5 average rating, 201 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
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
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 3 Oct
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
13–20 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 beds & pool
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.95 out of 5 average rating, 105 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
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 393 reviews
Top guest favourite
Flat in Islamorada
The HMH House
1 bedroom, 2 beds, 1 bathroom
12–17 Sept
4.97 out of 5 average rating, 58 reviews
Featured hotel
Room in Islamorada
One bedroom standard view suite two queens
3 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.96 out of 5 average rating, 79 reviews
Superhost
Flat in Tavernier
When Paradise is Key: Tropical Oceanfront Condo
2 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.88 out of 5 average rating, 102 reviews
Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 123 reviews
Guest favourite
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds, 2 bathrooms
15–20 Sept
4.99 out of 5 average rating, 68 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
Top guest favourite
Home in Key Largo
Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool
3 bedrooms, 4 beds, 3 bathrooms
28 Nov – 3 Dec
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki bar
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
17–24 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Oct
4.98 out of 5 average rating, 62 reviews