Features
Map
Rates & Availability
Review
Features
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PETS
No Pets Allowed -
BEACH
Beach Sun Loungers Beach Towels On The Beach -
DINING
Dining Table -
SAFETY
Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property) -
BEDROOM
3 Bedrooms Bed Sheets Provided Sofa Bed -
GENERAL
Double-glazed Windows Eco-friendly Cleaning Products Used Recycling Uses Some LED Lighting Waste Recycling Policy -
KITCHEN
Dishwasher Ice Maker Microwave Oven Paper Towels Refrigerator Spices Stovetop Toaster -
LAUNDRY
Laundry Facilities Washing Machine And Dryer -
PARKING
Car Required Electric Car Charging Station On Site Onsite Parking -
INTERNET
Free WiFi -
OUTDOORS
Balcony Barbecue Grill Dock Garden Outdoor Furniture -
POOL/SPA
Fence Around The Pool Heated Pool Shared/communal Pool -
BATHROOMS
2.5 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided -
LANGS SPOKEN
English -
THINGS TO DO
Basketball Nearby Birdwatching Nearby Boat On Site Cycling Nearby Ecotours Nearby Fishing Nearby Fitness Center Golfing On Site Kayak On Site Marina Nearby Parasailing Nearby Pickleball Court Tennis On Site Water Skiing Nearby Water Sports Equipment Water Tubing Nearby -
ENTERTAINMENT
Books DVD Player Games Netflix Streaming Services Smart TV With Cable/satellite Service -
LIVING SPACES
Fireplace Living Room -
CLIMATE CONTROL
Air Conditioning Heating -
FAMILY FRIENDLY
Children's Books Children's Dinnerware Children's Games Children's Toys Highchair Stair Gate -
LOCATION HIGHLIGHTS
In A Village In The City Center Near A Health Or Beauty Spa Near A Hospital Near A Zoo Near The Ocean Near The Sea On The Waterfront -
SERVICES AND CONVENIENCES
Iron/ironing Board Phone -
SUITABILITY/ACCESSIBILITY
Smoke-free Property
Map
Rates & Availability
Review
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Beth H.
Submitted Jan 26, 2026
Stayed Jan 10, 2026We had a very nice stay at Windley Cottage. Roger & Linda were very nice to work with. They responded quickly to all our questions before our trip and checked in with us during our stay to make sure we had everything we needed.
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Rene D.
Submitted Dec 9, 2025
Stayed Nov 29, 2025The home was absolutely beautiful. We loved our stay. The kitchen was fully stocked, the rooms were beautiful, the location was perfect, the hosts were welcoming and so easy to work with. The only downside was the listing says oceanfront, so I thought the home was on the ocean. It isn’t, it is in an oceanfront community, but the home sits one or two rows off the ocean, with no ocean view.
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Shannon L.
Submitted Dec 7, 2025
Stayed Nov 22, 2025The property was clean and well kept. The community is beautiful and the amenities were so useful. Having the dock on site was a dream for my boat loving family!
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Darrell P.
Submitted Aug 6, 2025
Stayed Jul 26, 2025Overall a good trip. A few items needed to be taken care of, but it didn't stop us from having a great time.
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Lisa F.
Submitted Jul 11, 2025
Stayed Jun 21, 2025We had a very nice stay at Windley Cottage. Roger & Linda were very nice to work with. They responded quickly to all of our questions prior to our trip and checked in with us during our stay to make sure we had everything we needed.
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Kent W.
Submitted Jun 10, 2025
Stayed May 31, 2025Great property. Very clean and had everything we needed. The whole complex is very nice and loved our stay. Owners very good with communication and friendly.
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P H.
Submitted May 31, 2025
Stayed May 24, 2025Spent a week in Islamorada with my wife, child (2 yrs) and we spent the majority of the time around the pool and getting some good RnR in.Check-in process was easy and the owners were very responsive. While the location was great, as we were pretty much glued to the pool and beach area, we didn't fully explore all that the area had to offer - but what we DID have to explore was great! Pool was perfect for our family activities, a quick (30-second) walk to the pool and beach area. Additionally, it's a quick 3-4 minute drive to Publix and a Starbucks, and another minute or two beyond that for a CVS/Pharmacy so some of the creature-comforts were close at hand.We would definitely come back to this condo, hopefully venturing out more to take advantage of the fishing and exploring more of the restaurants and area entertainment.
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Kim K.
Submitted May 24, 2025
Stayed May 17, 2025We had a 100% positive experience at this property. The home was beautiful both indoors and out—comfortable, clean, and thoughtfully maintained. Being in a gated community gave us an added sense of comfort and peace of mind. The pool was definitely our favorite spot, and we loved how conveniently close it was to the house. We also really enjoyed meeting and chatting with the other renters and owners—such a friendly and welcoming atmosphere. We’d absolutely stay here again and highly recommend it!
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harry s.
Submitted May 10, 2025
Stayed May 3, 2025Lodgings first rate. Boat access to Mahi and Grouper catches.
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Emily C.
Submitted Apr 26, 2025
Stayed Apr 19, 2025We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!
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Michelle H.
Submitted Apr 5, 2025
Stayed Mar 29, 2025Wonderful, well-maintained, clean home in paradise! Roger and Linda communicated before, during and after our stay to make sure everything was perfect. Morning coffee on the porch, lunch by the pool, and several delicious restaurants for dinner, nearby. Our teens had plenty to do from swimming, to fishing in the boat basin, and fishing charters out of Key Largo. A day trip to Key West is also very manageable. We loved the daily manatee visits to the boat docks on the property. A safe, quiet gated community that really is a place we hope to visit again very soon!
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Amy V.
Submitted Mar 29, 2025
Stayed Mar 22, 2025We just spent a week at Windley Cottage and had an amazing time. The house was very clean and comfortable for our family of 4. Everything was comfortable and we felt very safe and at ease in the community. The property was centrally located to what the keys have to offer. Communicating with Roger and Linda was so easy and they were more than helpful with questions we had. I would stay here again in a heart beat and recommend it to anyone.
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Kenneth C.
Submitted Mar 23, 2025
Stayed Mar 15, 2025Rodger and Linda is home and Islamorada is wonderful. They are unbelievably accommodating property owners and made the trip extra special. I look forward to returning and staying there again.
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Michael W.
Submitted Mar 2, 2025
Stayed Feb 22, 2025We've visited Angler's Reef many times over the years and haven't been let down yet. First time in Linda's & Roger's home. It is a very nice home; furnishings nice, appliances all work, home was just as described. Owners were easy to communicate with; converted twins to King and arranged dock access for us in advance. I'd highly recommend to anyone.
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Leslie G.
Submitted Feb 23, 2025
Stayed Feb 15, 2025We had a great visit! Great central location and perfect amenities for our family! Enjoyed the pool, fishing at the docks, kayaking and the comfortable space and cleanliness! Hosts checked on us every step of the way and made everything super easy! Would highly recommend for sure!! We will be back!!
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Sue M.
Submitted Feb 15, 2025
Stayed Feb 8, 2025The house we stayed in was immaculate and so attractive-exactly as pictured. We felt very safe in the gated community. We used the kayaks and pool and walked the area frequently. We rented bikes and had great areas to ride in. This was a very quiet, relaxing vacation. Lots of waterside restaurants to enjoy. The owner, Roger, was a great communicator.
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Kathy R.
Submitted Feb 15, 2025
Stayed Feb 1, 2025We had a wonderful stay at this lovely condo! It was very clean and had a well-equipped kitchen. The host was incredibly responsive to our questions. I chose to communicate via email had responses in a timely manner. The check-in process was smooth. Another thing I loved, the neighbors were incredibly welcoming and helpful. Overall, we highly recommend this condo for a great stay in Islamorada!
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Maria C.
Submitted Feb 2, 2025
Stayed Jan 25, 2025We loved this beautiful home and surroundings. It was peaceful and quiet and very well situated for us. The hosts were attentive and communicated well. It was the most graceful neighborhood in the Keys! We will come back, definitely!
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Diane P.
Submitted Jan 28, 2025
Stayed Jan 18, 2025We very much enjoyed our stay at Windley Key. The house was well stocked, very clean and beds were super comfortable. Communication with Linda & Roger was great. The property was very clean, pool was great (nice & warm for our cool week) and the beach area is very nice.Would highly recommend this property!
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Jeffrey L.
Submitted Nov 25, 2024
Stayed Nov 16, 2024The Cottage was in a great location and had everything we needed for our stay. From the initial questions we had to our last day there, the owners were prompt and on top of everything. The cottage itself is beautiful and warmly decorated. We stayed the week before Thanksgiving but the owners had a some Christmas decorations up which made us feel at home. We will definatley stay at the cottage again.
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Phil T.
Submitted Nov 22, 2024
Stayed Nov 2, 2024As alway Anglers Reef is a great place to stay and offers fantastic amenities and accommodation. The only problem was that temperamental lock for the front door. However Roger was extremely good at letting us in and out throughout our stay.
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Anita O.
Submitted Jul 1, 2024
Stayed Jun 22, 2024Great house, great community, great location. The kayaks, pool and dock for fishing were enjoyed by our group of six families, including 3 generations in multiple houses. Publix, restaurants and other activities are close by. The owner is extremely responsive and took care of an A/C issue quickly, even though it was after business hours.
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Roger W.
Submitted Jun 2, 2024
Stayed May 25, 2024Very nice