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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
8–14 Sept
5.0 out of 5 average rating, 16 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, 11 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
15–22 Sept
5.0 out of 5 average rating, 55 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds
1–8 Sept
New place to stay
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
5–12 Sept
4.97 out of 5 average rating, 219 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds
1–8 Sept
New place to stay
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds
12–19 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
1–7 Sept
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds
9–14 Oct
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 11 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, 75 reviews
Flat in Tavernier
Tavernier large private apartment with kitchen
1 bedroom, 1 bed
6–11 Sept
New place to stay
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds
7–12 Sept
4.95 out of 5 average rating, 105 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
7–12 Sept
4.93 out of 5 average rating, 391 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
1–8 Sept
New place to stay
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories, Views & Dock
3 bedrooms, 7 beds
4–11 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Apartment in Tavernier
Turtle Nest 1 Private beach,Pool, 2bed 2bath
2 bedrooms, 2 beds
7–12 Sept
4.91 out of 5 average rating, 139 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
1–6 Sept
4.8 out of 5 average rating, 5 reviews