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Vacation Rentals near Islamorada Dive Center

84001 Overseas Hwy, Islamorada, Florida 33036-3408
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    Travelers to Islamorada are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 676 Rentals in Islamorada
    Anglers Reef Islamorada Florida Sleeps 61 / 25
    0.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    BEACON REEF 3101 / 21
    (6)Excellent
    0.1 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    0.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Recently Renovated Luxury Townhome in Islamorada, Florida Keys1 / 23
    (1)Excellent
    2.9 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedroom Private Oceanfront House - Sol1 / 11
    (25)Very good
    1.8 miles from Islamorada Dive Center
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Islamorada Island Getaway1 / 30
    (2)Excellent
    1.6 miles from Islamorada Dive Center
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Oceanfront Anglers Reef Islamorada Florida Keys1 / 2
    (3)Very good
    0.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Delightful, wonderfully appointed home, perfect for a family of 4
    Reviewed March 24, 2018
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Lovely place to stay
    Reviewed August 24, 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
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    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    The "Nest" villa - 2Bed /2Bath, Stunning Bay Views, private sun deck, boat dock!1 / 30
    1.7 miles from Islamorada Dive Center
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    STUNNING CONDO with BALCONY/POOL in Oceanfront Building in beautiful Islamorada!1 / 30
    3.3 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!1 / 30
    (8)Very good
    2.9 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Great Place! Spacious 2/2 retreat with ocean views in the heart of the Keys.1 / 24
    3.9 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Paradise * Islamorada1 / 29
    (5)Excellent
    2.9 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Secluded Stunning Oceanview Townhome1 / 30
    (39)Excellent
    4.0 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Sunsets at Islamorada, Florida Keys. 2/2 Townho1 / 10
    2.9 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    BEACON REEF 5031 / 27
    1.0 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    About this property
    MINIMUM STAY: 28 DAYS This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit everyone's preference. Dine in...
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED1 / 24
    6.0 miles from Islamorada Dive Center
    3 Bedrooms, 3 Bathrooms, Sleeps 3 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 3
    Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach1 / 30
    (143)Excellent
    0.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 2
    132 Anglers Reef Monthly Rental- POOL, DOCK1 / 19
    0.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi1 / 18
    (57)Very good
    9.2 miles from Islamorada Dive Center
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    5/27-6/3 REDUCED $800! 3BR OceanFRONT, Panoramic Views, Huge Decks, Opt'l slip1 / 30
    (92)Excellent
    0.8 miles from Islamorada Dive Center
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Coral Cove Resort - a fisherman's dream1 / 30
    (14)Excellent
    3.3 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada1 / 30
    (75)Excellent
    6.0 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    GATED LUXURY ESTATE INCLUDES 5 STAR CHEF ON 2 ACRES PRIVATE WHITE SAND BEACH1 / 30
    (3)Excellent
    4.4 miles from Islamorada Dive Center
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
    Mitchell's Bayview Villa - Islamorada House on the Bay1 / 26
    (22)Excellent
    1.7 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Breathtaking ocean views for your Paradise vacations1 / 30
    1.4 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage1 / 30
    (32)Excellent
    10.1 miles from Islamorada Dive Center
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock1 / 30
    3.4 miles from Islamorada Dive Center
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Deep Water Canalfront Home W/ Boat Ramp1 / 15
    (8)Very good
    10.0 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS1 / 26
    (21)Very good
    9.7 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    � Casa 157 * White Marlin Beach1 / 30
    9.7 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Heated Pool Oceanside Home with 70' Seawall - Perfect Location1 / 15
    6.0 miles from Islamorada Dive Center
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Brand New / Totally Renovated Luxurious Home New To Rental Market.1 / 30
    (40)Excellent
    7.7 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!1 / 30
    (119)Excellent
    0.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedroom Private Oceanfront House - Bahia1 / 10
    (28)Very good
    1.7 miles from Islamorada Dive Center
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    5 Star Modern Oceanfront Islamorada Townhome on the Beach!1 / 30
    (57)Excellent
    4.0 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    WATERFRONT COTTAGE GREAT RATES !1 / 26
    (75)Excellent
    2.0 miles from Islamorada Dive Center
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Water Front 3/3 Family and Boat Friendly Home, Great Views1 / 26
    (29)Excellent
    10.3 miles from Islamorada Dive Center
    3 Bedrooms, 3 Bathrooms, Sleeps 3 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 3
    GREAT LOCATION !!! White Marlin Beach House, Islamorada1 / 26
    (65)Excellent
    9.7 miles from Islamorada Dive Center
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!1 / 24
    (58)Excellent
    1.5 miles from Islamorada Dive Center
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada1 / 30
    (54)Very good
    0.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.1 / 23
    (3)Excellent
    1.7 miles from Islamorada Dive Center
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.1 / 29
    0.9 miles from Islamorada Dive Center
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Amazing Sunsets on Sandy Beach, Pier, Pool, Bikes, Kayaks, Snorkeling, 2 Offices1 / 30
    (33)Excellent
    2.9 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 24
    (51)Excellent
    1.7 miles from Islamorada Dive Center
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Lower Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Oceanfront condo REMODELED 3/2 pool steps from balcony MM80 on ocean!1 / 30
    (8)Excellent
    3.4 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun1 / 25
    (35)Excellent
    2.0 miles from Islamorada Dive Center
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Your own Sunset from our own Private Balcony Directly over the Bay1 / 22
    2.9 miles from Islamorada Dive Center
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    Large Waterfront Home with Dockage In Islamorada, Florida Keys1 / 30
    7.5 miles from Islamorada Dive Center
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Your Home Away From Home! Relaxing Unit. Near Miami International Airport!1 / 26
    0.2 miles from Islamorada Dive Center
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Ocean Front 5 Bedroom Estate in the Heart of Islamorada1 / 30
    4.0 miles from Islamorada Dive Center
    5 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 5
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