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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
9–14 Aug
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4.93 out of 5 average rating, 387 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 50 reviews
Superhost
Flat in Islamorada
Isla Santorini | Islamorada Waterfront Condo, Pool
2 bedrooms, 3 beds, 2.5 bathrooms
3–10 Aug
New place to stay
Guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
4.89 out of 5 average rating, 27 reviews
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
9–15 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
5.0 out of 5 average rating, 15 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 75 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.95 out of 5 average rating, 104 reviews
Guest favourite
Home in Islamorada
Boat slip included August-November 2026!
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
4.92 out of 5 average rating, 50 reviews
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 68 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 147 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Flat in Marathon
Marina View Escape | Pool, Tiki & Breakfast
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Apartment in Islamorada
A Slice of Islamorada Paradise with Ocean Views
2 beds, 1 bathroom
1–6 Aug
Guest favourite
Flat in Key Largo
5. Key Largo Waterfront Studio | Kayak & Reef
1 bedroom, 3 beds, 1 bathroom
1–6 Aug
4.84 out of 5 average rating, 275 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 3 reviews