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Islamorada
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$1,000+
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Kid friendly (91)
Elder access (39)
Pet friendly (27)
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Parking (79)
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Water Views (43)
Waterfront (31)
Ocean Views (22)
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121 rentals
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100' Private Beach Front Ocean Front Estate
2 reviews
4 bedrooms
4 bathrooms
Sleeps 12
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Ocean-Front Caribbean Home.
2 reviews
3 bedrooms
3 bathrooms
Sleeps 8
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January 10% OFF! Boat Slip included, 2 Beaches, Pool, Oceanfront Anglers Reef
77 reviews
2 bedrooms
3 bathrooms
Sleeps 6
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2 Acres on the Atlantic Ocean in Islamorada, Florida
3 bedrooms
3 bathrooms
Sleeps 6
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Mitchell's Bayview Villa - Islamorada House on the Bay
19 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Islamorada Florida Cozy Cottage
3 bedrooms
3 bathrooms
Sleeps 4
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Mitchell's Keys Villa - Private, Secluded House on the Bay
42 reviews
1 bedroom
1 bathroom
Sleeps 4
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SUNSHINE PLACE
16 reviews
1 bedroom
1 bathroom
Sleeps 3
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BROCK HAUS ON THE GULF
22 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
101 reviews
2 bedrooms
3 bathrooms
Sleeps 4
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Luxurious Home at beautiful Anglers Reef with Boat Slip available
81 reviews
2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip
104 reviews
3 bedrooms
3 bathrooms
Sleeps 8
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Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef
77 reviews
2 bedrooms
3 bathrooms
Sleeps 6
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Islamorada Waterfront Paradise Getaway!
32 reviews
1 bedroom
1 bathroom
Sleeps 2
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A little Piece of Heaven to wash your worries away
29 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Anglers Reef with Boat Slip, Pool, Ocean
26 reviews
2 bedrooms
3 bathrooms
Sleeps 5
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This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2 Sleeps 6
39 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental
28 reviews
3 bedrooms
3 bathrooms
Sleeps 8
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Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable
28 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Bayside Condo, marina, pool and beach
17 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Newly refinished condo open water views very nice
7 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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75731 Overseas Highway
13 reviews
4 bedrooms
4 bathrooms
Sleeps 10
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Completely Remodeled 2 Bedroom, 2 Bath Florida Keys Condo On the Atlantic Ocean
12 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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SANCTUARY IN PARADISE
7 reviews
4 bedrooms
4 bathrooms
Sleeps 10
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Oceanfront Oasis - Pinch me am I dreaming!!!
5 reviews
5 bedrooms
6 bathrooms
Sleeps 12
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BEACON REEF 310
6 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Luxury condo overlooking harbor with ocean view
6 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!
5 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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140 Atlantic Lane
8 reviews
5 bedrooms
4 bathrooms
Sleeps 10
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Paradise Beach Sandy Oceanfront
4 reviews
4 bedrooms
4 bathrooms
Sleeps 10
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76004 Overseas Highway
5 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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132 Columbus Drive
17 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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82754 Overseas Highway
4 reviews
5 bedrooms
3 bathrooms
Sleeps 10
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Bay Front Beauty/ Summer Sea Must See!!!!
4 reviews
1 bedroom
1 bathroom
Sleeps 4
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137 LeSerra Lane
9 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool
3 reviews
5 bedrooms
4 bathrooms
Sleeps 12
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Come relax in Islamorada, the tropical jewel of the Florida Keys!!
3 reviews
1 bedroom
1 bathroom
Sleeps 4
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LITTLE BAY - Upper Duplex
3 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.
3 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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LITTLE BAY - Lower Duplex
4 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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VILLA RIOLO
3 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Islamorada - PARADISE FOUND 3 bedroom/2 bath
3 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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PALMS 309
3 reviews
2 bedrooms
2 bathrooms
Sleeps 5
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Islamorada Waterfront Paradise 2
5 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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LITTLE BAY - Cottage
3 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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BEACON REEF 222
2 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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MANATEE MANOR
2 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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Windy Cove #1
2 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Mile Marker 87 - Mina Bay - Oceanfront 'Million Dollar View'
2 reviews
2 bedrooms
2 bathrooms
Sleeps 8
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Little Bay Compound
2 reviews
5 bedrooms
6 bathrooms
Sleeps 18
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