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Islamorada Vacation Rentals

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    Travellers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 29 Rentals in Islamorada
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    Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available1 / 41
    (24)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip1 / 24
    (97)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach1 / 49
    (22)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Luxurious Home from Home in Amazing Anglers Reef with Boat Slip available1 / 50
    (68)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    A little Piece of Heaven to wash your worries away1 / 23
    (22)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach1 / 22
    (14)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Anglers Reef Home Boat Dock Available1 / 24
    (33)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach1 / 48
    (98)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Anglers Reef- May Discount!  Book Now!1 / 24
    (29)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Tropical Islamorada Bungalow with pool, beach cruiser bikes, and free Wi-Fi1 / 50
    (105)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool1 / 48
    (73)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach1 / 30
    (77)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Brand New / Totally Renovated Luxurious Home New To Rental Market.1 / 44
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    'Pleasant Palms' An Oceanside Condo In Downtown Islamorada In The Florida Keys1 / 25
    (12)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Completely Remodeled 2 Bedroom, 2 Bath Florida Keys Condo On the Atlantic Ocean1 / 23
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Sauna
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    COASTAL ELEGANCE FOR RENT IN ISLAMORADA !!! PARADISE FOUND ON DEEP WATER1 / 49
    (56)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Anglers Reef Islamorada 2/2.5 great family home oceanfront community1 / 17
    (31)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    5 Star Review, Book Early for 2020 - Anglers Reef Oceanfront Community1 / 49
    (61)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 61 / 30
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef1 / 33
    (64)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Large Bedrooms and 2.5 bath Oceanfront/VIEWS- DOCK INCL Anglers Reef Islamorad1 / 27
    (30)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Islamorada Sunsets, 2 Beaches, Pool, WiFi, Cable, Bikes, & More1 / 41
    (28)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 24
    (34)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK*1 / 43
    (6)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Mitchell's Bayview Villa - Islamorada House on the Bay1 / 26
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    DIRECT OCEAN FRONT JEWEL, Private Heated Pool,70 Ft Dock,Best Deal Around!!!!!1 / 31
    (28)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Tropical Paradise in Venetian Shores.  Luxury Heated Pool / Spa, 4 Bikes & Kayak1 / 23
    (20)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Islamorada, Florida Keys 33166
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Islamorada, Most Popular Florida Key1 / 15
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Gorgeous Waterfront Home Minutes From Downtown Islamorada1 / 19
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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