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Bedrooms 2
Half Baths1
Property type house
Minimum Stay 7 nights


About the property

2 Bedroom, 2.5 Bathroom, sleeps 6

Relax in tranquility at "Windley Cottage", located at 129 Anglers Way in Angler's Reef, Islamorada's premier gated oceanfront community. With two luxurious and spacious bedrooms, each with its own full en-suite bathroom, this single-family, private home offers many amenities. Whether you're looking for a quiet getaway or a fun-filled ocean experience, our home is perfect for families or couples traveling together.

If you are bringing a boat, we can assist with docking arrangements in Anglers Reef (additional fee). Nearby marinas have available docking and boat/jet ski rentals as well. The Alligator Reef Lighthouse and Islamorada's Holiday Isle Sandbar are just off-shore.

We provide our guests with two sit-in kayaks and needed equipment. Launch them from one of our two private beaches and head out to the famous sandbar for an afternoon of swimming and socializing. Swim in the resort-style pool overlooking the Atlantic Ocean or stroll around the lushly landscaped grounds among the pastel "Bahamian conch cottages". Explore the area with our complimentary twin "beach-cruiser" bicycles.

Enjoy the SLIDESHOW below for a TOUR of Windley Cottage and the Anglers Reef community.

Islamorada is known as 'The Sport fishing Capital of the World', and fishing opportunities and water activities are limitless. Fine dining, unique shops and spas as well as area attractions, like "Theater of the Sea" and the Morada Way Art Walk draw visitors from all over the Keys to Islamorada, Village of Islands.

Our home sleeps six people comfortably. It offers one king bedroom with a private covered porch and a guest bedroom with two twin beds (convertible to a king). Each bedroom has its own on-suite bath and spacious shower. Watch the sunrise over the ocean as you sit on the balcony off the second bedroom. A sleeper sofa completes the sleeping accommodations.

On the first floor, relax on the front or enjoy an ocean view from the rear porch. A comfortable living room, dining area, powder room, and fully equipped kitchen with stainless steel appliances, subway tile backsplash, and granite counters complete the tastefully-decorated interior of the home. The well- equipped kitchen has all of the cookware, dishes, and small appliances you need for meal preparation. Our new upscale stainless steel kitchen appliances were installed in August 2016.

Children are welcome and we provide a highchair/booster seat, playpen, and baby gate for the stairs to accommodate the very young ones. We also provide pool toys, board games, and a variety of books. But vacationers' pets are not allowed in Anglers Reef.

You won't even need to pack beach towels, chairs, or noodles. Just pack a few clothes and your toothbrushes and come on down to enjoy the wonderful Florida Keys with comfortable, luxurious accommodations in our home, Windley Cottage. See why people from all over the world get sand in their toes and return here over and over again.

Be sure to enjoy the SLIDESHOW TOUR of the inside and outside of the cottage at the bottom of the listing (just below "Amenities"): Also check out "DISCOVER ISLAMORADA ( which provides a great short overview of the Village of Islands.

Islamorada Vacation License # VR-058, D.B.P.R. State Vacation Rental DWE5403337.

More Details

Roger and Linda Robitaille
Member since: 2015
Premier Partner

This HomeAway partner has demonstrated and is committed to fast response times, the best rates, and a great traveler experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
January 18, 2018

About Roger and Linda Robitaille

Having grown up in Western Massachusetts, we both graduated with Masters Degrees from the University of Massachusetts, Amherst. For many years, we vacationed in South Florida over the holidays and yearned for its warm weather and gorgeous ocean waters. Now, our permanent residence is in Naples, Florida, where we enjoy boating and cycling all long.

Roger and Linda Robitaille purchased this house in 2015

Why Roger and Linda Robitaille chose Islamorada

Having become acquainted with all of the Keys during business travel over the years, I came to appreciate all that Islamorada has to offer. We dreamed of owning a home here. Angler's Reef, with its quaint, well-maintained conch homes and gorgeous landscaping captured our hearts! "Windley Cottage" had the perfect location - close to the pool and boat lagoon, yet farther from the road.

What makes this house unique

It was love at first sight! Windley Cottage is an architectural style known as a "Bahamian Conch Cottage" which features high ceilings, lots of porches, metal roof, double-hung windows, and pastel painted clapboard siding. It is reminiscent of the classic structures of Key West. Although each of the homes has different individual details (dormers, gingerbread, hip or gabled rooflines, porch railing details), all are of the same style, providing the feeling of a Village within the Village. A stroll through the community is a step back to simpler, more laid-back times (but with all the modern amenities). Sitting on the back porch or on the guest room balcony looking at the ocean is a treat! That's why we're here and want you to enjoy our home just as much as we do!


Islamorada House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Included
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 6
  • Max. adults: 4
  • Min. age of primary renter: 25 ...
  • Children welcome ...
  • Parties/events not allowed ...
  • Pets not allowed ...
  • Non smoking only ...
  • Guests must be respectful of the home, items in the home, and neighbors.
  • Quiet hours are 10:00P.M. - 6:00A.M.
  • If you find anything broken or if something breaks during your stay, you must let us know immediately so that we can repair it. Insurance covers it!
Location Type:
  • Ocean View ...
  • Oceanfront
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Free Wifi
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • 1 Half Bath
  • Half bath on first floor - toilet , Self-closing toilet seat.
    Master Bathroom - toilet , shower , Large shower. Self-closing toilet.
    Guest Bathroom - toilet , shower , Large shower. Self-closing toilet.
  • On-suite bathrooms for both bedrooms feature spacious walk-in showers with glass doors and granite vanity countertops. The powder room has a pedestal sink.
  • 2 Bedrooms, Sleeps 6
  • Sleeper sofa - 1 sleep sofa /futon , In great room on first floor.
    Master Bedroom - 1 king , Chest of drawers, bench at base of bed, and two night stands
    Guest Bedroom - 2 twin/ single , Twin beds convert to a king bed, dresser and night stand.
  • Second floor Master has 1 king bed with private covered porch, on-suite bathroom, and walk-in closet. The guest room has two twin beds (convertible to a king)and a walk-in closet, and on-suite bathroom. Enjoy a sunrise ocean-view on the balcony. Queen sleeper on the first floor near the half-bath.
  • Books ...
  • DVD Player ...
  • Games ...
  • Music Library ...
  • Satellite / Cable ...
  • Television ...
  • Toys ...
  • Balcony ...
  • Bicycles ...
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • 2 bicycles
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • festivals
  • marina
  • museums
  • playground
  • recreation center
  • reefs
  • restaurants
  • water parks
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • hiking
  • jet skiing
  • paragliding
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • swimming
  • water skiing
  • water tubing
  • wind-surfing
Infant's booster seat with tray, playpen, and gate for stairway. Sand toys, folding beach chairs, baby pool, and noodles are provided for a great day at our private beaches. Several nearby boat launches for those who tow a boat or jet ski and storage for the trailer. Housekeeping is exit cleaning. Additional cleanings must be arranged through owner.


Wonderful! 4.8/5 -
(41 traveler reviews)

85% Complete
12% Complete
0% Complete
0% Complete
2% Complete
average rating of 4.780488 based on 41 reviews
Ann Arbor Michigan

Beautifully appointed home with very responsive owners

  • 5 of 5

Our family rented three homes in Anglers Reef and Windley Key surpassed all expectations. The home is child ready which was perfect for our son and his young children. The owners obviously love their home and that shone through on all of our conversations with them from the initial to closing contacts. We would highly recommend this home.

  • Submitted: Jan 9, 2018
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
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Bloomfield Hills, Michigan

Beautifully maintained house

  • 5 of 5

Roger and Linda are first-rate hosts. They responded promptly to our questions (we wondered about hurricane damage) and emailed information exactly when we needed it. They maintain the house in beautiful condition. We were happy guests.

  • Submitted: Dec 31, 2017
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
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Simply amazing!

  • 5 of 5

Quaint, beautiful, well-maintained. Low key, quiet atmosphere.

  • Submitted: Oct 11, 2017
  • Stayed: October 2017
  • Source: HomeAway
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Perfect in every sense!

  • 5 of 5

Roger and Linda's Windley Cottage was the perfect getaway for our family. It is obvious that they really care about this place. The house is extremely well appointed with high quality furnishings throughout. Angler's reed is very well placed on Islamorada and one of the most private and upscale communities. The house is very clean, very well stocked with high quality linens, towels, kitchenware etc. Both bedrooms are very roomy and comfortable. It looks and feels brand new. Would definitely return!

  • Submitted: Sep 1, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Beautiful home and location!

  • 5 of 5

Our family just returned from a week and we loved it! Decor was beautiful, location amazing, weather was perfect. It exceeded our expectations and we will be back for years to come. The Islamorada sand bar is a 5 min boat ride and diving reefs are very close. We rented a boat for the week from a marina close by (they actually delivered the boat to our dock) and we snorkeled, fished, lobsters from islamorada to key largo. Amazing vacation and home.

  • Submitted: Aug 20, 2017
  • Stayed: August 2017
  • Source: HomeAway
Owner's Response: Jeff and Alexis, So glad you had the perfect vacation in our Windley Cottage. Its close proximity to the sandbar and diving reefs provides additional opportunities for enjoying our amenities. We look forward to welcoming your family back! Linda and Roger
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Ormond Beach fl

Serious Issues

  • 1 of 5

When we arrived the Refrigerator was not working. We called Roger and he insisted that it was. We called back after he requested that we simply wait for a few hours and it was still not cooling. I understand that the last thing that you want to believe is that your appliances aren't working but Roger insisted that we were wrong. We had a weeks worth of groceries refrigerated medications etc. and we were asked to wait after bottled water was still warm after 5 hours in the refrigerator. This was on saturday. No one came out on sunday and we were called by the sears company to be available on monday between 9-12. Again no one showed up. At this point I'm on vacation managing the repairs on this home. Refrigerator was repaired Tuesday cause as described by repair man was power surge or outage stopped the fan. We had also called about the washing machine not completing cycles again told that it works. We are all in our late thirtys and early fortys so constantly being told that everything works when it clearly did not is not only inconvenient but also infurating. The repair guy figured out that if you put the washer on and close the door on the closet that the machine is in it continues to fill but never runs the cycle. Then came thursday we returned from the boat and the Air conditioning was out. Again Roger insisted that we obviously do not know how to work an air conditioner. Repair guy had to come out because the outside unit had stopped working. Roger and Linda were nice enough to offer to treat us to dinner for all the inconveniences that we had during our stay. When I sent them the receipt they of course balked at it and refused to treat the other couple that rented the house with us even though the reservation clearly shows 4 adults a toddler and my 6 yr old. I was shocked when going on Homeaway to find that after the refrigerator instance they changed our reservation to their own email address thus eliminating the trip from my account so we were not even afforded the satisfaction of leaving a review. My dealings with this couple were fantastic until something in the house isn't working and then I felt that I was being treated as a child in my Parents home. Roger assumed that we had no idea how basic appliances worked and we were uncapable of determining that something was wrong. I received the email from Roger refusing to pay for the dinner that he offered and then scolding me for not letting him know that one of his bike tires was flat.

  • Submitted: Aug 18, 2017
  • Stayed: July 2017
  • Source: HomeAway
Owner's Response: These guests had a cursed vacation week. It started out before they even arrived when they had a flat tire along the Interstate! We had stayed at the Cottage the previous week and left early on Saturday, their arrival date, because they said they’d like to arrive early and we wanted to accommodate them. When we left the home, all of our refrigerated food was very cold and the refrigerator was running fine. Upon their arrival, our vacationers phoned to tell us that the refrigerator was not cooling. It, like all of our kitchen appliances, is less than one year old. Once we had determined that the refrigerator wasn’t going to cool our guests’ food, we contacted the manufacturer, Sears™. The contact at Sears™ said they would arrange for a repair visit on Monday. We provided the repairman access codes so that the guests could enjoy their vacation and not have to wait around and we let them know they didn’t need to be there. The repairman came out on Monday at 1:00 PM and he determined that a sensor under warranty had failed and that he would order one, pick it up on the mainland and install it on Tuesday, which he did. During this time, our vacationers told us that the clothes washer was not working properly and kept shutting off. The Sears™ serviceman took a look at it and determined that the door knob was hitting the on/off switch when the laundry closet door was closed by the vacationers. We never had this problem before because other guests haven’t closed the door when washing laundry so as to hear the alarm when the cycle is complete. There was nothing wrong with the machine. The repairman slid the stacked washer/dryer back a bit and the problem was solved. On Thursday, around 4:30 PM, we got a call from our guests that the A/C was not working when they returned from a day at out. They said the fan was blowing but the air was warm. The A/C had just received its semi-annual service two weeks before. They told us they were heading out to dinner. We called our A/C service company and they had the system running by around 6:00 PM that night, so our vacationers returned to a cool house. What they don’t know and we didn’t tell them was that we had lined up accommodations for them at a very nearby resort just in case the A/C couldn’t be fixed that day. This was not easy, as that week was “Mini Lobster Week”, the busiest week of the year in the Keys, and accommodations are scarce and at their highest prices of the year. (More ...)
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Nearest Airport
76 Miles
Miami International Airport
Nearest Barpub
0.5 Miles
Hog Heaven, Smuggler Cove, Ocean View
Nearest Golf
33 Miles
Key Colony Beach Par-3 Golf Club
Nearest Restaurant
0.5 Miles
Hog Heaven, Smuggler Cove, Ocean View
Nearest Beach
0.05 Miles
Angler's Reef
Car: necessary


Theater of the Sea

History of Diving Museum

The only remaining drawbridge on the FL Keys (Snake Creek)

Alligator Reef lighthouse and its famous sandbar

Windley Key Fossil Reef Geological State Park

Boat and jet ski rentals at Snake Creek Marina

The Rain Barrel "Village of Artists"

Founders Park

Fishing charters- Robbie's or Bud and Mary's Marinas

John Pennekamp State Park

Tarpon feeding at Robbie's Marina

Morada Way Arts & Cultural District (MM 81.5, 3rd Thursday monthly)

2008 HGTV Dream Home Location (at end of Gimpy Gulch Road next to the Rain Barrel Village of Artists)


Islamorada Fish House

Lazy Days

Marker 88



Island Grill

Hog Heaven

Green Turtle

Smugglers' Cove

Midway Cafe

Mango Mike's

Midway Cafe

Bob's Bunz

Mrs. Mac's Kitchen

... and many more!


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Property Damage Protection $59
Exit Cleaning fee (+Tax) $159 + Tax
Tax Rate 12.5%


Boat slips in Angler's Reef are available to rent by the week at $250. Boats of up to 31 feet can be accommodated.

If you book through them, will assess an additional "Service Fee" to your invoice. Like the Property Damage Protection insurance, this is payable to them directly, not to the property owner.

Payment in US$ only. Payment by other than U.S. - issued Credit Cards subject to additional processing fee of 3% of the charges.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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