OCEANSIDE ANGLERS REEF HOME- Gated Community with Pool, Dock, Private Beach

Islamorada, Florida
$413 avg/night Minimum Stay 7 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 7 nights

Min Stay

Windley Cottage is a welcoming, tastefully-decorated home located at mile marker 85. It's away from the highway, and just steps from the pool and docks. The “Bahamian conch style home provides irresistible charm and comfort tucked in among lush landscaping. Angler's Reef is centrally located, perfect for exploring all of the Florida Keys!
Whether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer! Flexible bed arrangements. Call 239-250-4135 for more information. I
We have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our complimentary paddle boards or kayaks. Cycle to the many gift shops and restaurants. Scuba or snorkel the nearby coral reefs and shipwrecks, rich with underwater wonders. Dive near the popular Alligator Reef Lighthouse, which is visible and easily accessible from Angler's Reef. For a fee, dock your boat in our protected lagoon with direct, deep-channel access on the Atlantic. Nearby marinas offer boat/jet ski rentals, fishing/scuba/snorkeling charters, and party boats for fun on the water. Whether you fish from shore or our docks, flats-fish in the back bays, or deep-water fish for big game, Islamorada has it all! Swim with the dolphins and learn about the local marine life at Theater of the Sea (1/2 mile from our home). Dine at one of the fabulous nearby restaurants, many offering nightly entertainment.

Just 2 miles north is Islamorada Founders Park at MM 87 Bayside. The park offers a shallow water beach, ball fields, playground, fishing jetty, driving cage, 3 paddle ball courts, bocce, tennis, a large playground, basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park.

Other municipal parks include the Islamorada Library Beach and Anne’s Beach. The Windley Key State Geological Site, a state park, is a former coral rock quarry, where fossils of sea creatures can be seen throughout the park.

After a busy day, enjoy a glass of wine on one of our two private beaches. Play a board game on the back porch. Dim the pendant lights in the great room and turn on the fireplace as you cuddle up to watch your favorite movie after a busy day.

Just pack a few clothes and your toothbrush and head down to the Florida Keys for the vacation of a lifetime in the comfort and luxury of Windley Cottage! See why people from all over the world get sand in their toes and return here again and again!

Contactless check-in and check-out is on Saturdays. Please contact us if you want a different day. Our calendar is updated in real-time and posted rates are accurate.

STR#-24-0163
FL DBPR #DWE5403337

NOTE: We also own a vacation rental property on Cape Cod, MA. Visit Vrbo listing 3757615 for photos and further information of this property.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • 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

CheckIn Check-in : 05:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Beth H.

    Submitted Jan 26, 2026

    Stayed Jan 10, 2026

    We 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.

  • Rene D.

    Submitted Dec 9, 2025

    Stayed Nov 29, 2025

    The 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.

  • Shannon L.

    Submitted Dec 7, 2025

    Stayed Nov 22, 2025

    The 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!

  • Darrell P.

    Submitted Aug 6, 2025

    Stayed Jul 26, 2025

    Overall a good trip. A few items needed to be taken care of, but it didn't stop us from having a great time.

  • Lisa F.

    Submitted Jul 11, 2025

    Stayed Jun 21, 2025

    We 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.

  • Kent W.

    Submitted Jun 10, 2025

    Stayed May 31, 2025

    Great 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.

  • P H.

    Submitted May 31, 2025

    Stayed May 24, 2025

    Spent 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.

  • Kim K.

    Submitted May 24, 2025

    Stayed May 17, 2025

    We 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!

  • harry s.

    Submitted May 10, 2025

    Stayed May 3, 2025

    Lodgings first rate. Boat access to Mahi and Grouper catches.

  • Emily C.

    Submitted Apr 26, 2025

    Stayed Apr 19, 2025

    We 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!

  • Michelle H.

    Submitted Apr 5, 2025

    Stayed Mar 29, 2025

    Wonderful, 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!

  • Amy V.

    Submitted Mar 29, 2025

    Stayed Mar 22, 2025

    We 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.

  • Kenneth C.

    Submitted Mar 23, 2025

    Stayed Mar 15, 2025

    Rodger 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.

  • Michael W.

    Submitted Mar 2, 2025

    Stayed Feb 22, 2025

    We'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.

  • Leslie G.

    Submitted Feb 23, 2025

    Stayed Feb 15, 2025

    We 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!!

  • Sue M.

    Submitted Feb 15, 2025

    Stayed Feb 8, 2025

    The 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.

  • Kathy R.

    Submitted Feb 15, 2025

    Stayed Feb 1, 2025

    We 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!

  • Maria C.

    Submitted Feb 2, 2025

    Stayed Jan 25, 2025

    We 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!

  • Diane P.

    Submitted Jan 28, 2025

    Stayed Jan 18, 2025

    We 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!

  • Jeffrey L.

    Submitted Nov 25, 2024

    Stayed Nov 16, 2024

    The 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.

  • Phil T.

    Submitted Nov 22, 2024

    Stayed Nov 2, 2024

    As 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.

  • Anita O.

    Submitted Jul 1, 2024

    Stayed Jun 22, 2024

    Great 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.

  • Roger W.

    Submitted Jun 2, 2024

    Stayed May 25, 2024

    Very nice

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Total

Includes taxes and fees
$413+
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