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Vacation Rentals nearby Anne's Beach

Mile Marker 73.5, Lower Matecumbe Key, Islamorada, Florida 33036
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    Travellers to Islamorada are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 451 Rentals in Islamorada
    Islamorada Waterfront Paradise Getaway!1 / 28
    (32)Excellent
    2.1 kilometres from Anne's Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    1.8 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Luxury condo overlooking harbor with ocean view1 / 20
    (6)Excellent
    1.8 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • Waterfront
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    Pet friendly
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    Reviewed July 5, 2018
    Luxurious surroundings, plush bath towels, great view, modern everything, cold central A/C, great soft pillow-top bed & nice quality linens. And, did I mention the...
    Reviewed April 4, 2018
    We are avid lovers of the keys and returned to vacation here about 20 times. We have stayed at Bay Harbor 3 times, but this condo is really superior. First, Lee is an...
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    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    22.2 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.9 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Waterfront
    • Private Outdoor Pool (Heated)
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    About this property
    Villa (Half Duplex), three bedrooms / two bathrooms plus a loft and a crow's nest area with great views. Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. There is approximately 50' of deep-water dockage with access to...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedroom Private Oceanfront House - Sol1 / 10
    (25)Very good
    14.5 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Islamorada Island Getaway1 / 29
    (2)Excellent
    20.1 kilometres from Anne's Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    22.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Minimum Rental: 28 Days "West Plaza Del Lago" will steal your breath away the moment you pull into the drive way. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    SPECTACULAR SUNSETS AND FRESH OCEAN BREEZE AWAIT YOU IN ISLAMORADA, FLORIDA!1 / 29
    (8)Very good
    22.2 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    23.7 kilometres from Anne's Beach
    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
    22.2 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Secluded Stunning Oceanview Townhome1 / 29
    (39)Excellent
    23.8 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    22.2 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.9 kilometres from Anne's Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Minimum Rental: 1 MONTH Pelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving...
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    Layton, Long Key
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach1 / 29
    (143)Excellent
    19.0 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 2
    18.9 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi1 / 17
    (57)Very good
    2.6 kilometres from Anne's Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Truly OceanFRONT Home 3BR 2.5BA, Panoramic Ocean Views, Two 350+ sqft Decks1 / 29
    (92)Excellent
    18.8 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Coral Cove Resort - Fisherman's Dream1 / 29
    (14)Excellent
    12.1 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada1 / 29
    (75)Excellent
    27.1 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    GATED LUXURY ESTATE INCLUDES 5 STAR CHEF ON 2 ACRES  PRIVATE WHITE SAND BEACH1 / 29
    (3)Excellent
    24.6 kilometres from Anne's Beach
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
    Mitchell's Bayview Villa - Islamorada House on the Bay1 / 25
    (22)Excellent
    14.5 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage1 / 29
    (32)Excellent
    1.1 kilometres from Anne's Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock1 / 29
    (37)Excellent
    11.9 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Deep Water Canalfront Home W/ Boat Ramp1 / 15
    (8)Very good
    1.2 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS1 / 25
    (21)Very good
    1.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    1.7 kilometres from Anne's Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 4
    18.8 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    27.2 kilometres from Anne's Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Brand New / Totally Renovated Luxurious Home New To Rental Market.1 / 29
    (40)Excellent
    4.9 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Welcome to Paradise "Sandbar Bungalow Villa" * Anglers Reef1 / 29
    (119)Excellent
    19.0 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedroom Private Oceanfront House - Bahia1 / 10
    (28)Very good
    14.5 kilometres from Anne's Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    5 Star Modern Oceanfront Islamorada Townhome on the Beach!1 / 29
    (57)Excellent
    23.9 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    WATERFRONT COTTAGE GREAT RATES !1 / 24
    (75)Excellent
    14.1 kilometres from Anne's Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Water Front 3/3 Family and Boat Friendly Home, Great Views1 / 25
    (29)Excellent
    0.8 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 3 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 3
    GREAT LOCATION !!! White Marlin Beach House, Islamorada1 / 25
    (65)Excellent
    1.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    4 Bedroom House In Angler's Reef, Includes 31' Boat Slip1 / 29
    (74)Excellent
    19.0 kilometres from Anne's Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!1 / 23
    (58)Excellent
    14.9 kilometres from Anne's Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Anglers Reef Oceanfront Complex w Pool & Beach-Islamorada1 / 29
    (54)Very good
    18.9 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Cable/satellite TV
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.1 / 22
    (3)Excellent
    20.1 kilometres from Anne's Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.1 / 28
    (61)Excellent
    18.9 kilometres from Anne's Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Amazing Keys Sunsets, Sandy Beach, Pier Fishing, Pool, WiFi, & More at 10% Off1 / 29
    (33)Excellent
    22.2 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 23
    (51)Excellent
    14.5 kilometres from Anne's Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Oceanfront condo REMODELED 3/2 pool steps from balcony MM80 on ocean!1 / 29
    (8)Excellent
    11.9 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Waterfront
    • Hot Tub
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    Pet friendly
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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 / 24
    (35)Excellent
    14.1 kilometres from Anne's Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    22.2 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    Lower Matecumbe Key, Islamorada
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
    5.4 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    W AVAIL BOAT Separate & Together Duplex 70' Concrete Dock w Private BEACH1 / 29
    (10)Excellent
    1.7 kilometres from Anne's Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Lower Matecumbe Key, Islamorada
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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