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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
,
4.78 out of 5 average rating, 172 reviews
Flat in Islamorada
Poolside 2 queen Apartment
4.8 out of 5 average rating, 50 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Superhost
Flat in Islamorada
Isla Santorini | Islamorada Waterfront Condo, Pool
New place to stay, 2 bedrooms, 3 beds, 2.5 bathrooms
2–9 Aug
Top guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
4.89 out of 5 average rating, 27 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
5.0 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
4.97 out of 5 average rating, 67 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jun – 2 Jul
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
4.97 out of 5 average rating, 103 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Islamorada
Boat slip included August-November 2026!
4.92 out of 5 average rating, 50 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
5.0 out of 5 average rating, 54 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
29 Aug – 5 Sept
Guest favourite
Flat in Marathon
Brand New, Dock Front, Daily Breakfast + cleaning
4.96 out of 5 average rating, 23 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 3 bathrooms
9–15 Aug
Guest favourite
Home in Key Largo
Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool
4.89 out of 5 average rating, 47 reviews, 3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Superhost
Apartment in Islamorada
A Slice of Islamorada Paradise with Ocean Views
2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 216 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug