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Holiday Homes near 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 holiday rental today, and have the perfect trip.
    All 63 Rentals in Islamorada
    75130 Overseas Highway1 / 19
    (6)Excellent
    3.1 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    75731 Overseas Highway1 / 32
    (13)Very good
    3.9 kilometres from Anne's Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    76004 Overseas Highway1 / 35
    (5)Excellent
    4.3 kilometres from Anne's Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    132 Columbus Drive1 / 18
    (17)Very good
    5.3 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 1 April 2019
    132 Columbus Drive, Islamorada, FL is a beautifully remodeled place to stay right on the water. Great views from living room and both bedrooms. We spent most our time right...
    Reviewed 12 January 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
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    About this property
    Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in the house, you'll never want to leave. This 2 bedroom, 2 bath home has a great back porch, large yard, and shaded carport/ sitting area. Located in Lower Matecumbe, this house is close to downtown...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Oceanfront Oasis with Quintessential Island Living1 / 44
    (5)Excellent
    4.9 kilometres from Anne's Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    Despite our rainy week in Islandmorada, Sean helded to make our vacation seemless! We had 10 people staying with us to help celebrate my husbands 50th birthday. The house had...
    Reviewed 13 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
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    About this property
    ***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL PERIOD IS 7 DAYS*** For the ultimate Keys experience, little can compare to settling into a custom-built home boasting its own private beach. Crafted with pleasure in mind, this luxurious five-bedroom, four-and-a-half bath house...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 11
    1.8 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi.  The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedicated boat slip, a fish...
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    Long Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE1 / 16
    (9)Excellent
    3.0 kilometres from Anne's Beach
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Patio
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2017
    If you want a piece of heaven on earth? Stay at Casa Rio Islamorada. This quiet, restful and scenic waterfront paradise is the place for fun, love and romance. This place is in...
    Reviewed 9 February 2016
    We recently stayed at Casa Rio in Islamorada Florida, what a beautiful place. The apartment is located on a quiet residential cul de sac in a lovely part of Islamorada. The...
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    About this property
    The storm has passed and CasaRio Islamorada is awaiting your visit. We have lowered our rates to encourage more tourists into the area. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! Please enter 28 days into your request...
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    76300 Overseas Highway1 / 25
    (11)Very good
    4.8 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 31 July 2018
    Islamorada! Lower Matecumbe! Paradise! This older, ideally located, and well maintained property is a jewel. Since my dad first introduced me to Islamorada 45 years ago, I've...
    Reviewed 2 April 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails,...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Islamorada Waterfront Paradise Getaway!1 / 28
    (32)Excellent
    2.4 kilometres from Anne's Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2019
    My husband and I just left, and I already miss it! We loved the tiki hut, the kayaks, and watching the fish and manatees and birds. The furniture and hammocks in the tiki hut...
    Reviewed 15 March 2017
    We spent a wonderful, spirit rejuvenating MONTH with Ewa and Peter at their beautiful home by a lagoon in Lower Matecumbe Key. At first we bustled about, kayaking from the dock...
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    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! This is a very popular rental, so ask about your preferred dates early! This best Islamorada waterfront location, has quick easy access...
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    Islamorada, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    137 LeSerra Lane1 / 31
    (8)Very good
    5.0 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed 26 March 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the...
    Reviewed 5 June 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
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    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in  Lower Matecumbe (South part of Islamorada). This home is the second one in on a point  and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee  maker, toaster, and blender. There are...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.2 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****INQUIRE ABOUT OUR LAST MINUTE DISCOUNTS!! *** Welcome to your beach-front oasis on the bay side at mile marker 74 in Islamorada, the Sport Fishing Capital of the World. Dig your toes in the sand, bask in the warm, clean waters and soak up the sun at this beautiful, beach front retreat. Dock...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Incredible Luxury Home with Waterfront!! Paradise1 / 19
    (2)Excellent
    2.5 kilometres from Anne's Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 December 2017
    Cannot even express in words how great of an experience my family had! The house is unbelievable, with two apartments downstairs and three bedrooms upstairs. The yard is amazing...
    Reviewed 6 December 2017
    I loved having everyone at one location and with the 3 separate living areas, there was plenty of space! Easy access to a great bike/walking path. Great restaurants just a...
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    About this property
    Lo-Key Estate is truly a luxury Keys home situated on a private 400’ waterfront peninsula with the use of a tropical swimming pool w/waterfall and hot tub(shared w/guest house) There are Ocean Views from the 2 & 3rd floors. Lo-Key is a custom 5 bedroom/5 bath home that opens onto Florida Bay...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    140 Atlantic Lane1 / 49
    (8)Very good
    5.0 kilometres from Anne's Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 January 2015
    We seven people (3 couples and one single) stayed here for one week. This big house is located right on the Atlantic Ocean, but it has no beech. It has a great wraparound porch...
    Reviewed 13 August 2014
    The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
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    About this property
    You'll fall in love with this little piece of paradise. Amazing ocean views can be enjoyed from every room in this beautiful home and separate guest quarters. With an open concept living, kitchen and dining room, a large wrap around porch, 5 bedrooms and 4 bathrooms, this house has everything you...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    1.7 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM. NO EXCEPTIONS Nautilus Getaway is a stunning 3bed/3bath single family home located in Islmorada.  The interior of this home is casual elegance and well-appointed throughout. The kitchen has all appliances that are upgraded and the kitchens flow through design is...
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    Layton, Long Key
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5.6 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Washer
    • Waterfront
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada.  The condo has a designated 4 car covered parking.  Quick boating access to the Ocean or the Gulf of Mexico thru the Channel 5 Bridge.   The beauty of the bridge can be seen right...
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    Layton, Long Key
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL IS 7 DAYS*** Overlooking the ocean, this luxurious Islamorada condo, located at Mile Marker 75, combines inspiring Atlantic views with easy access to boating, diving or just taking in the sun and sand. Indoors, guests will enjoy a...
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    Layton, Long Key
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.8 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL IS 7 DAYS*** Luxurious condo located at Mile Marker 75 on the Bayside in Islamorada. Watch the stars come out as evening turns to night from this top-flight unit at Mile Marker 75 on Islamorada’s bayside. During the day enjoy...
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    Layton, Long Key
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.5 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great deep dockage and quick access to bay and ocean!!! Beach & Bay Bungalow. This home has it all. New 65' 4k HD television and high speed wireless interntet included. All bedrooms have flat screen television. Spectacular long water views from inside and out of this secluded estate property!...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Oceanfront Islamorada Home with Private Beach - Great for Kite Surfing!1 / 24
    (2)Average
    1.5 kilometres from Anne's Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Beautiful four bedroom, Ocean Front home with...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.8 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse (this unit does not have Wi-Fi inside the condo) . The condo boasts some amazing views of the Clear Blue...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 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 4 April 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
    3.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.1 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Bay Harbour A-304- 7 night minimum1 / 34
    (12)Very good
    1.8 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed 1 May 2016
    There is no beach but the pool is not crowded. A hot tub is near-by. This unit,304A was very nicely decorated. Loounge chairs make watching TV comfortable. Kitchen pans...
    Reviewed 5 January 2015
    This condo was great for us...3 couples(family) each having their own bedroom..2 1/2 bathrooms ...we used the kitchen and 5 people could work together in it! The kitchen was...
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    About this property
    Beautiful 3 bedroom and 2.5 bath luxury penthouse condo located at mile marker 74.5 bayside.  This condo is nicely decorated, fully appointed, and very spacious for you and your family. The unit has a beautiful screened-in lanai off the living room and master bedroom with brand new furnishings to...
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    Long Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.9 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise Beach *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Enjoy incredible beach and ocean views from this family-friendly, waterfront retreat. This home features a beautiful, sandy backyard...
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    Layton, Long Key
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    4.7 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    'The Beach Fixes Everything'. That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Islamorada Waterfront Paradise 21 / 29
    (5)Very good
    3.0 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2016
    House was nice - except we did not feel comfortable - could not feel at ease - felt like we were being watched - paid a lot of money
    Reviewed 23 April 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
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    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Paradise Beach Sandy Oceanfront1 / 46
    (3)Excellent
    3.9 kilometres from Anne's Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Waterfront
    • Hot Tub
    • Terrace
    • Washer
    • Ocean Views
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2019
    My family just spent a fun filled week in Islamorada and our accommodations at Paradise Beach were fantastic! The house is impeccably designed with a pool that kept us outside...
    Reviewed 20 April 2019
    The house is beautiful, views are amazing, and it has everything you need or will ever need. Our whole family enjoyed a week of relaxation, and we spent some memorable time...
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    About this property
    Endless open water views with spectacular sunrises and sunset colored skies await in this private gated estate. Sink your toes into the natural sand beach. Enjoy your privacy at the heated pool and spa among lush tropical vegetation and palm trees. This Key West styled house offers stunning...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Islamorada Luxury Waterfront Condo with Boat Slip1 / 21
    (20)Excellent
    1.9 kilometres from Anne's Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This was probably the nicest place we have stayed in the Keys! It had 2 master bedrooms! 2 1/2 baths. The place is very roomy. Can park car underneath the condo. They have ice...
    Reviewed 28 March 2019
    The condo was gorgeous; it is always nice when what your see advertised in pictures is what you get when you arrive at the rental property. Views from the screened in patio of...
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.9 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    Enjoy a getaway in one of Islamorada's most prestigious neighborhoods when you rent this three-bedroom, three-bathroom home. Located at the end of a cul-de-sac within the Port Antigua neighborhood on Lower Matecumbe Key, the home quickly enchants arriving guests with its peach-colored exterior set...
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    Long Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Beautiful Bayside View with Swimming Pool1 / 49
    (1)Excellent
    3.2 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    My family just LOVED this house. The backyard is amazing with a beautiful view and plenty of space for boat-dockage. My family had fun paddle boarding, kayaking, and...
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    About this property
    Bayside View is truly an amazing Florida Keys home, with great Bay views from all floors! Bayside View is a 3 bedroom/3 bath home that is directly on the Florida Bay. This location satisfies all of your fishing & water sport desires. The home is completely renovated and absolutely gorgeous. The...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    OCEANFRONT pool30'Dock,7niteMin, 6ppl max,sorry no pets STANDADrate$465/nite1 / 51
    (6)Excellent
    4.9 kilometres from Anne's Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2014
    We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
    Reviewed 14 February 2014
    My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to...
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    About this property
    FOR ADDITIONAL REVIEWS GO TO 'HOMEAWAY.COM' LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, NO PETS, RENTAL...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    100' Private Beach Front Ocean Front Estate1 / 42
    (2)Excellent
    3.9 kilometres from Anne's Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2018
    INCREDIBLE HOME ON THE BEACH!This beachfront home offered more amenities than any other home we have rented for vacation. Complete game room as well as kayaks and paddle...
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    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 people with room to spare....
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    1.8 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Near the house...
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    Long Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.6 kilometres from Anne's Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WELCOME TO PARADISE! Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous panoramic ocean views from every room....
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    1.6 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Not your typical Florida Keys home. With antique furnishings and modern touches, this home is truly a masterpiece. This newly renovated home offers a large, open concept layout with a gorgeous kitchen, modern dining room and cozy living room. With stainless steel appliances, a unique entertainment...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5.5 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    The dream home away from home. The upstairs main floor offers two large bedrooms with cozy king beds, two full baths, a beautifully decorated open concept living and dining room, updated kitchen and great outdoor living area. Pool and canal views from not only the expansive screened-in balcony, but...
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    Location Information
    Layton, Long Key
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1.9 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
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    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.0 kilometres from Anne's Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Safety Harbour Canalfront Home. Fabulous protected dockage right outside your home! This canalfront home consists of a 3 bedrooms and 2 bathrooms upstairs along with an open concept living room, dining room and kitchen with the 4th bedroom and bath located on the ground level with it's own private...
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    Location Information
    Layton, Long Key
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    MY PARADISE1 / 25
    (6)Excellent
    1.1 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Balcony
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 December 2018
    An amazing beach house on one of the only sandy beaches in the Florida keys, and our new favorite Florida vacation spot! Pet friendly, sun sand & surf at your doorstep, a...
    Reviewed 14 August 2018
    We fell in love with Sunset Drive the first time we stayed. My Paradise was our first choice but was already rented during the time we wanted, so we stayed elsewhere. The next...
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    About this property
    <b> Minimum Rental: 28 Days </b> 'My Paradise' is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.1 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    The best of both worlds, with stunning ocean views from the balcony and protected deepwater dockage acrross the street this home is a true gem. This great home offers two bedrooms and two bathrooms, an open concept living room, dining room and kitchen and a back porch where you can sip margaritas...
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    Location Information
    Layton, Long Key
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    SUNRISE ON SUNSET1 / 26
    (1)Excellent
    1.3 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2019
    We have been renting here for the last 10, 15 years, lost count. Great location and a great family house to enjoy with your kids and grandkids. Great boat basin and the owner is...
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    <b> MINIMUM STAY: 28 DAYS </b> 'Sunrise on Sunset' is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level area. This spacious 3BR/3BA* single family home offers...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    2.2 kilometres from Anne's Beach
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, canalfront, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The downstairs only of this house is rented. Super cute 1 bedroom. Great ground level home for those that do not do stairs....
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    Location Information
    Long Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
    CASA DORADO1 / 24
    (2)Excellent
    4.6 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2018
    This is the third time we have stayed at Casa Dorado. It is a beautiful home in an amazing location. If you like fishing, boating,diving, snorkling, and amazing sunsets this is...
    Reviewed 10 June 2017
    Beautiful home with great access to boat launch and dockage at the house. Very neat and clean and every amenity you could want. Had some AC problems that Keys Holiday Rentals...
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    About this property
    <b> Minimum Rental: 28 Days </b> 'Casa Dorado' is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2.3 kilometres from Anne's Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>Minimum Rental: 1 Month </b> Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    BLUE WATER RETREAT1 / 26
    (3)Very good
    4.7 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
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    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2017
    We recently returned from a month long vacation stay at Blue Water Retreat and it was so hard to leave! This house is situated on an ocean canal with spectacular ocean views...
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    <b> Minimum Rental: 28 Days </b> 'Blue Water Retreat' is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    4.9 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Patio
    • Ocean Views
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WE ARE A WONDERFUL WATERFRONT HOME IN THE HEART OF ISLAMORADA FLORIDA! WATCH THE MANATEES AND TARPON- WEEKLY STAYS ARE WELCOME, WE ARE FULLY LICENSED FOR WEEKLY STAYS. NEW SAMSUNG HD 4K TELEVISION, PRIVATE PROTECTED DOCKAGE. DIRECT OCEAN ACCESS, NEWLY PAVED PRIVATE ROAD. HIGH SPEED WIRELESS...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    VILLA RIOLO1 / 22
    (2)Excellent
    5.2 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    We have stayed in many places, this is one of our favorites by far. Great location, great fishing. Very clean and well kept. Has a private boat ramp which was very important...
    Reviewed 14 August 2014
    Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
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    About this property
    <b> Minimum Rental: 28 Days </b> 'Villa Riolo' is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.9 kilometres from Anne's Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2.8 kilometres from Anne's Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 3 Bathrooms, Sleeps 6 MINIMUM STAY REQUIRED - NOT A SHORT TERM RENTAL - PLEASE CONTACT US FOR SPECIFIC DATES, AVAILABILITY AND RATES. Every time we stay, we never want to leave. 3 story bayside villa with its own beach. Great location. Views of both the Bay and the Ocean. Three good...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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