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Vacation Rentals near Robbie's of Islamorada

77522 Overseas Hwy, Islamorada, Florida 33036-3813
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    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 807 Rentals in Islamorada
    Recently Renovated Luxury Townhome in Islamorada, Florida Keys1 / 23
    (1)Excellent
    3.4 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedroom Private Oceanfront House - Sol1 / 11
    (25)Very good
    1.3 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Islamorada Island Getaway1 / 30
    (2)Excellent
    2.1 miles from Robbie's of Islamorada
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada1 / 30
    4.3 miles from Robbie's of Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Upper Matecumbe Key, Islamorada
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2Bed / 2Bath Villa, Marina, Boat ramp, Sun terrace, Water views & Pet friendly!1 / 30
    1.2 miles from Robbie's of Islamorada
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    STUNNING CONDO with BALCONY/POOL in Oceanfront Building in beautiful Islamorada!1 / 30
    3.8 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!1 / 30
    (8)Very good
    3.4 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    A Great Place! Spacious 2/2 retreat with ocean views in the heart of the Keys.1 / 24
    4.4 miles from Robbie's of Islamorada
    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
    3.4 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Secluded Stunning Oceanview Townhome1 / 30
    (39)Excellent
    4.5 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sunsets at Islamorada, Florida Keys. 2/2 Townho1 / 10
    3.4 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED1 / 24
    6.5 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    132 Anglers Reef Monthly Rental- POOL, DOCK1 / 19
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Upper 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
    8.7 miles from Robbie's of Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Port Antigua Waterfront Home With Private Beach Access1 / 17
    8.9 miles from Robbie's of Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Mitchell's Bayview Villa - Islamorada House on the Bay1 / 26
    (22)Excellent
    1.2 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Breathtaking ocean views for your Paradise vacations1 / 30
    0.9 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Sea Glass Cottage Beautiful Canal Front Home1 / 30
    7.8 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS1 / 26
    (21)Very good
    9.3 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!1 / 28
    (119)Excellent
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Star Modern Oceanfront Islamorada Townhome on the Beach!1 / 30
    (57)Excellent
    4.5 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    WATERFRONT KEYS COTTAGE GREAT RATES ! Walking distance to world famous Lorelei1 / 26
    (75)Excellent
    1.5 miles from Robbie's of Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Upper 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
    9.8 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    GREAT LOCATION !!! White Marlin Beach House, Islamorada1 / 26
    (65)Excellent
    9.2 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Vacation Condo at Futura Yacht Club1 / 30
    (66)Excellent
    4.4 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.1 / 23
    (3)Excellent
    2.2 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.1 / 29
    (61)Excellent
    1.4 miles from Robbie's of Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Upper 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
    3.4 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront condo REMODELED 3/2 pool steps from balcony MM80 on ocean!1 / 30
    (8)Excellent
    2.9 miles from Robbie's of Islamorada
    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 Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach1 / 30
    (143)Excellent
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    SEP/OCT reduced 3BR 2.5BA OceanFRONT Wide Ocean Views Huge Decks Yaks/SUPs Dock1 / 30
    (92)Excellent
    1.3 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Coral Cove Resort - a fisherman's dream1 / 30
    (14)Excellent
    2.8 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada1 / 30
    (75)Excellent
    6.5 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage1 / 30
    (32)Excellent
    9.6 miles from Robbie's of Islamorada
    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
    (37)Excellent
    2.9 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Deep Water Canalfront Home W/ Boat Ramp1 / 15
    (8)Very good
    9.6 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    � Casa 157 * White Marlin Beach1 / 30
    9.2 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Brand New / Totally Renovated Luxurious Home New To Rental Market.1 / 30
    (40)Excellent
    7.2 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip1 / 30
    1.4 miles from Robbie's of Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedroom Private Oceanfront House - Bahia1 / 10
    (28)Very good
    1.3 miles from Robbie's of Islamorada
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!1 / 24
    (58)Excellent
    1.0 miles from Robbie's of Islamorada
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Hot Tub
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    Upper Matecumbe Key, Islamorada
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 24
    (51)Excellent
    1.2 miles from Robbie's of Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun1 / 25
    (35)Excellent
    1.5 miles from Robbie's of Islamorada
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Sunset from our own Private Balcony Directly over the Bay1 / 23
    3.8 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Terrace
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    Upper Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    Keys Kottage1 / 44
    (2)Excellent
    1.2 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Parking
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    Paradise
    Reviewed May 1, 2022
    Absolutely everything about this property is beautiful. The cottage is more than I could have hoped for & had everything we needed, the patio, the boat dock, trailer parking...
    Paradise Found...
    Reviewed May 13, 2018
    Islamorada is our place. It's the perfect combination of activities: relaxation, shopping, restaurants, fishing, boating, etc.. We have been coming to the Keys for about 10...
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    About this property
    Keys Kottage Villa, a waterfront property located on Florida Bay, at mile marker 82 in a native hammock in the heart of beautiful Islamorada in the Florida Keys. It is the perfect site for a fisherman's dream vacation! Offered is not only free parking for your car or truck, but also for your...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront 2/2 Condo in Beacon Reef - Free boat dock1 / 4
    0.5 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Central Heating
    • Ocean Views
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    About this property
    Enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE In the fishing capitol of the world, Islamorada. Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to beautiful grounds. Only this floor has the stairs, others have to go through a...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed1 / 20
    1.2 miles from Robbie's of Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Upper Matecumbe Key, Islamorada
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    W AVAIL BOAT Separate & Together Duplex 70' Concrete Dock w Private BEACH1 / 30
    (10)Excellent
    9.2 miles from Robbie's of Islamorada
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Location Information
    Lower Matecumbe Key, Islamorada
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Beautiful Waterfront Port Antigua Home, Pool, Private Beach1 / 30
    8.9 miles from Robbie's of Islamorada
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Your Keys Getaway - A1 / 17
    9.3 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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