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Search results; Over 1,000 homes in Islamorada

Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.95 out of 5 average rating, 105 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds
9–15 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds
18–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
12–19 Sept
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
9–14 Sept
4.93 out of 5 average rating, 392 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
20–26 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Escape - Ocean Front Villa - Sleeps 10
3 bedrooms, 10 beds
14–19 Sept
4.87 out of 5 average rating, 181 reviews
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds
24–29 Sept
4.96 out of 5 average rating, 142 reviews
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds
19–26 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds
13–18 Sept
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds
11–16 Oct
5.0 out of 5 average rating, 100 reviews
Guest favourite
Villa in Key Largo
Twilight #32 Key Largo 4BR Villa | Pool,
4 bedrooms, 4 beds
28 Sept – 3 Oct
4.8 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds
15–20 Oct
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Key Largo
Ocean view, seaside paradise with golf cart.
3 bedrooms, 4 beds
13–18 Sept
4.93 out of 5 average rating, 76 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds
9–16 Sept
5.0 out of 5 average rating, 23 reviews