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Vacation Rentals near Rain Barrel Village

86700 Overseas Hwy, Mile Marker 86.7, Bayside, Islamorada, Florida 33036-3138
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    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 276 Rentals in Islamorada
    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 32
    (3)Excellent
    0.9 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    1.2 miles from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 38
    (4)Excellent
    0.8 miles from Rain Barrel Village
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    LYONS LANDING1 / 25
    (1)Excellent
    1.0 miles from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    Reviewed June 27, 2017
    Every room is comfortable,charming and the property managed to make you feel comfortable and at home..with every amenity..including an ice maker..so nice to have here in The...
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    About this property
    Minimum Rental: 28 Days 'Lyons Landing' is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and...
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1.0 miles from Rain Barrel Village
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    0.3 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    About this property
    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely...
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!1 / 42
    (8)Very good
    0.4 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.4 miles from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87 Our Islamorada beach modern decorated townhome is waiting for you. It’s a two story unit and third level loft; 2 Bedroom/2 Bath - sleeps 8. Next door is Founders Park & Plantation Yacht Harbor. A private gated community with 24hr...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    0.5 miles from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach1 / 35
    (140)Excellent
    1.5 miles from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Brand New / Totally Renovated Luxurious Home New To Rental Market.1 / 46
    (40)Excellent
    10.2 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef1 / 31
    (117)Excellent
    1.5 miles from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    4.2 miles from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable1 / 51
    (33)Excellent
    0.4 miles from Rain Barrel Village
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 24
    (51)Excellent
    4.2 miles from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Islamorada, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.0 miles from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Park Model mobile home located oceanside on beautiful Windley Key in Islamorada, Florida Keys, the 'sport fishing capital of the world.' This is a great spot for relaxing, fishing and/or exploring the Keys, situated 75 miles from Miami and 85 miles from Key West. 1 BR plus upstairs sleeping or...
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    Islamorada, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    10.0 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 61 / 34
    (55)Excellent
    3.3 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Maison #3071 / 44
    (7)Excellent
    5.9 miles from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    12.1 miles from Rain Barrel Village
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    12.1 miles from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.9 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    5.9 miles from Rain Barrel Village
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Wonderful 1 Bedroom Condo with Pool & Bay Views - Summer Seas #4201 / 29
    (2)Excellent
    1.4 miles from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    2.2 miles from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Stunning 3 Bedroom Bayfront Home - 194 Airstream Lane1 / 35
    (2)Excellent
    1.2 miles from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.5 miles from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    4.7 miles from Rain Barrel Village
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
    2.2 miles from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Beautiful Oceanfront Property with Pool -- Alligator Reef - Conch & Lobster1 / 49
    (6)Very good
    2.0 miles from Rain Barrel Village
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Private Tropical Oceanfront Estate with Pool and Beach1 / 50
    (31)Excellent
    9.7 miles from Rain Barrel Village
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.1 / 19
    (15)Excellent
    11.5 miles from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    12.2 miles from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2.4 miles from Rain Barrel Village
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Charming 2 Bedroom Canalfront Home in Islamorada1 / 22
    (1)Average
    10.1 miles from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage1 / 36
    (9)Excellent
    1.0 miles from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Wonderful 3 Bedroom Oceanfront Townhome with Pool - Windy Cove #11 / 19
    (6)Very good
    2.4 miles from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 miles from Rain Barrel Village
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    0.7 miles from Rain Barrel Village
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    *Searenity Beach House*  - Ocean Front Home with Views of the Atlantic Ocean1 / 24
    (5)Excellent
    11.0 miles from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool1 / 50
    (94)Excellent
    1.5 miles from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3.3 miles from Rain Barrel Village
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    1.2 miles from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    3.5 miles from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    6.2 miles from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Great 4 Bedroom Home with Breathtaking Bay Views - 76004 Overseas Highway1 / 35
    (5)Average
    10.6 miles from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.4 miles from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Cable/satellite TV
    • Terrace
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Oceanfront, Pool, Dock... Checks all the boxes!1 / 50
    (3)Very good
    10.2 miles from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    12.7 miles from Rain Barrel Village
    7 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 15
    9.1 miles from Rain Barrel Village
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Location Information
    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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