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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, 3 bathrooms
8–14 Sept
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews
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Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
7–13 Sept
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
13–20 Sept
4.91 out of 5 average rating, 23 reviews
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Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
5–12 Sept
4.97 out of 5 average rating, 219 reviews
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Guest favourite
Home in Key Largo
Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
5 bedrooms, 9 beds, 3 bathrooms
13–18 Sept
4.99 out of 5 average rating, 158 reviews
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Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
17–24 Sept
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds, 3.5 bathrooms
24–31 Oct
5.0 out of 5 average rating, 13 reviews
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Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
8–13 Sept
4.8 out of 5 average rating, 5 reviews
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Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 13 reviews
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Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
2–9 Sept
5.0 out of 5 average rating, 15 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
8–15 Sept
New place to stay
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Top guest favourite
Apartment in Tavernier
Toes in the Sand - 2 Bedroom Condo Sleeps 4
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.86 out of 5 average rating, 271 reviews
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Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
18–25 Sept
5.0 out of 5 average rating, 17 reviews
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Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
1–6 Sept
New place to stay
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Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
8–15 Sept
New place to stay
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Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
1–8 Sept
New place to stay