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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 private bathroom
23–28 Nov
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4.96 out of 5 average rating, 151 reviews
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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
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Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
16–23 Sept
5.0 out of 5 average rating, 12 reviews
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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, 35 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds
8–15 Sept
New place to stay
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Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
5–12 Sept
4.97 out of 5 average rating, 219 reviews
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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, 17 reviews
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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
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Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds
1–6 Sept
4.96 out of 5 average rating, 141 reviews
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Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds
7–12 Sept
4.92 out of 5 average rating, 13 reviews
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Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds
5–10 Oct
4.98 out of 5 average rating, 61 reviews
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Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds
13–18 Sept
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Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
24 Apr – 1 May
5.0 out of 5 average rating, 56 reviews
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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
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Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds
1–8 Sept
New place to stay
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Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
1–6 Sept
New place to stay
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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
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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
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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