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Bedrooms 2
Separate WC's1
Space 0 sq ft
Property type house
Minimum Stay 7 nights


About the property

2 Bedroom, 2.5 Bathroom, sleeps 6


Anglers Reef is Islamorada’s premier gated, oceanfront community of 52 private, single-family homes, located at mile marker 85 on Windley Key. Come stroll around its lushly landscaped grounds and “Bahamian conch cottages”, a unique and relaxing environment. Swim in the oceanfront resort-style pool which is kept at 87degrees year-round. Enjoy a sunset or sun-bathe on the east beach. Launch our two complimentary sit-in kayaks from the west beach for an afternoon of swimming and socializing at the famous “Holiday Isles Sandbar”.

Dock your boat in our protected lagoon with direct ocean access (slips are available for rent upon request at booking for boats up to 31 feet). Islamorada is known as the “Sport Fishing Capital of the World”, and fishing opportunities are limitless. The Alligator Reef Lighthouse is visible and easily accessible from Anglers Reef. Whether you fish from shore, flats-fish in the back bays, or deep-water fish for big game fish, Islamorada has it all! Nearby marinas offer boat ramps, boat/jet ski rentals, fishing/scuba/snorkeling charters, and head boats for fun on the water.


Relax in tranquility at “Windley Cottage”, located at 129 Anglers Way. Our welcoming, tastefully-decorated home is away from the highway and just steps from the pool. It offers three porches, a balcony, and two luxurious, spacious bedrooms, each with its own en-suite bathroom. Whether you’re looking for a quiet couples’ retreat or an exciting ocean experience with the family, our home is perfect!

Windley Cottage boasts endless amenities for adults and children alike! Enjoy ocean views from the back porch and guest room balcony. Watch the sun rise over the ocean as well as a sunset from the guest balcony. The living room, with ample, comfortable seating, offers an HD television, Blu-Ray™/DVD player, books, games, and puzzles for those down times.

The fully-equipped kitchen features up-scale stainless steel appliances, a subway tile backsplash, and granite countertops. The kitchen has all the conveniences of home. The counter-top appliances, dishes, glassware and a large assortment of utensils make meal preparation easy and enjoyable. Stools at the kitchen counter allow seating for a quick breakfast or snack. The dining area, with the table and chandelier provide that laid-back atmosphere for a peaceful meal after a busy day. An electric grill is provided on the back porch off the kitchen. The cheery powder room rounds out the first floor.

Our home sleeps six people comfortably with its two bedrooms and sleeper sofa. The Master bedroom has a King bed, two dressers, and a nightstand, as well as an HD TV with built-in DVD player. The guest bedroom has one dresser and two twin beds that convert to a King bed upon request, creating a second Master for couples traveling together. Enjoy a morning cup of coffee watching the sunrise and a sunset glass of wine from the guest balcony.


Windley Cottage is child-friendly! We provide a highchair/booster seat, Pak-N-Play™, a baby gate for the stairs, and a baby splash pool to accommodate the very young ones. The complimentary kayaks and bikes, pool toys, board games, and a variety of books and activity books will entertain the older children. There’s no need to bring beach towels, folding chairs, or noodles. We have it all for you! Just pack a few clothes and your toothbrush and head down for the Florida Keys 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!

Be sure to enjoy the SLIDESHOW TOUR of the inside and outside of the cottage at the bottom of the listing (just below "Amenities"): https://youtu.be/E1AK91sgcU8. Also check out "DISCOVER ISLAMORADA" (https://youtu.be/_3EnsgsTxB0) which provides a great short overview of the Village of Islands.

Vacationers' pets are not allowed in Anglers Reef.

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

More Details

Roger and Linda Robitaille
Member since: 2015
Premier Partner

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

Speaks English
Response time:
Within an hour
Response rate:
Calendar last updated:
19 May, 2018

About Roger and Linda Robitaille

We both grew up in Western Massachusetts. 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 power-boating and bicycling all year 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, Roger came to appreciate all that Islamorada, especially Windley Key, has to offer and 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. It was love at first sight!

What makes this house unique

Windley Cottage, in an architectural style known as a "Bahamian Conch Cottage", features high ceilings, lots of porches, metal roof, double-hung windows, and pastel yellow 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 basic 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 our home is special and we want you to enjoy our home just as much as we do!


Accommodation and facilities for this holiday house in Islamorada in Monroe County

Property Type:
  • house
  • Self-catering
  • Housekeeper Included
Floor Area:
  • 0 sq ft
House Rules:
  • Check-in: 16:00
  • /
  • Check-out: 11:00
  • 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:
  • near the sea ...
  • Ocean View ...
  • Water View ...
  • 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 ...
  • Hob ...
  • Toaster ...
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • 1 Separate WC
  • Half bath on first floor - Toilet , Self-closing toilet seat.
    Master Bathroom - Toilet , Shower Enclosure , Large shower. Self-closing toilet.
    Guest Bathroom - Toilet , Shower Enclosure , Large shower. Self-closing toilet.
  • En-suite bathrooms for both bedrooms feature spacious walk-in showers with glass doors and granite vanity countertops. The powder room has a pedestal sink and headboard trim.
  • 2 Bedrooms, Sleeps 6
  • Sleeper sofa - 1 Sofa bed/Futon , In great room on first floor.
    Guest Bedroom - 2 Single Bed , Twin beds convert to a king bed, dresser and night stand.
    Master Bedroom - 1 Extra Lg. Double Bed , Two dressers, bench at base of bed, and a night stand
  • Second floor Master has 1 king bed with private covered porch, en-suite bathroom, and walk-in closet. The guest room has two twin beds (convertible to a king)and a walk-in closet, and en-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 ...
  • Terrace ...
  • Kayak / Canoe ...
  • Garden ...
  • Barbecue ...
  • 2 bicycles
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • bay
  • botanical garden
  • churches
  • cinemas
  • festivals
  • library
  • marina
  • museums
  • playground
  • recreation centre
  • reefs
  • restaurants
  • theme parks
  • water parks
  • zoo
Leisure Activities:
  • antique hunting
  • 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
  • diving
  • snorkelling
  • bay fishing
  • surf fishing
  • swimming
  • water skiing
  • water tubing
  • wind-surfing
Twin beach cruiser bikes provided. Infant's booster seat with tray, Pack N' Play©, gate for stairway. Sand toys, folding beach chairs, baby pool, and noodles are provided for a great day at our private beaches. We provide a start-up kit with shampoos, conditioners, soaps, sponge/scrubby, dish machine cubes, and single-use clothes washer soap powder. 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 -
(51 traveller reviews)

86% Complete
11% Complete
0% Complete
0% Complete
1% Complete
average rating of 4.8039217 based on 51 reviews

Wonderful home

  • 5 of 5

Everything was perfect, would definitely stay there again!

  • Review Submitted: 29-Apr-2018
  • Date of Stay: April 2018
  • Source: HomeAway
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Outstanding. The rental property, location, pool and interaction with the owners were GREAT.

  • 5 of 5

We had a great vacation. The location was perfect and the property was very spacious and clean. The owners were outstanding to work with. They communicated with us prior to, during and even after our stay. During our trip, there was a water main break on the island. The owners went over and above to keep us constantly informed during the water outage which was very helpful and appreciated. I would recommend this property to anyone looking for rental in Islamorada.

  • Review Submitted: 14-Apr-2018
  • Date of Stay: April 2018
  • Source: VRBO, from HomeAway
Owner's Response: We're pleased you enjoyed your stay your stay in Windley Cottage. We pride ourselves on maintaining our property and when unforeseen things happen, such as the water main break, we do everything possible to stay on top of the situation and keep our guests informed along the way. We look forward to your next visit.
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Mechanicsburg, PA

Perfect Beach House in a great location on Windley Key

  • 5 of 5

The owners are amazing- very responsive to your needs. From the beginning, the communication was excellent. I like how they give you tips on where the grocery stores are, good places to rent boats/ bikes, etc. and even when the drawbridge goes up!

The house itself is the perfectly decorated beach house- I love the decor but still kid-friendly, although I would say if my kids were toddlers, I might have been a bit worried about the steep stairs but I know others who had toddlers have reviewed the place favorably as well. My kids are 10 and 12 y.o. And it was perfect for them.

The owners have so many amenities- even sunblock and shaving cream so if you forget something, they have you covered and they even have some coffee etc in a welcome pack so you can wait until the next day to go grocery shopping. In the kitchen, they have every item you can think of - even a griddle!

I like too that they have a cleaning service ( fee included) so you don't have to spend the last day of vacation cleaning the house like some other VRBO rentals.

The location was perfect - quieter area but still plenty of restaurants nearby and fun activities, starting with the pool and sandbar beach. We rented a 2 person kayak. Unfortunately, we didn't use their kayaks because someone had caused damage to those and the first time we went out, one of the kayaks took on water and submerged quickly. But the owners were really awesome about it as soon as we let them know- they even ordered a new one but it didn't arrive while we were here but they offered to pay for another rental- we had other activities planned so we didn't take them up on it but WOW, what amazing owners. Truly, these are people who will make sure you have a great vacation. To date, I have to say these owners are the best I've ever dealt with on VRBO.

They also provide 2 bikes and we rented two for the kids. I will say the traffic is pretty bad around here so we mostly biked early in the morning when the traffic was minimal.

For the kids, they have everything you can think of- even high chairs for little ones. My kids made good use of the many games (scrabble, uno, poker), books, jigsaw puzzles. There are tour guides, brochures, coupon books, and the Audobon society book on flora and fauna. And there are tons of towels, extra linens, pillows, etc.

I can't say enough about this house, location, amenities and awesome owners. We will definitely be back!

  • Review Submitted: 31-Mar-2018
  • Date of Stay: March 2018
  • Source: VRBO, from HomeAway
Owner's Response: We are glad that you and your family had such a great time at Windley Cottage and that you appreciated the amenities and information about we provide to our guests. We pride ourselves on being responsive to the needs of our travelers. Realizing that many vacationers are unfamiliar with what Islamorada has to offer, we make every effort to inform them of things we think will be of interest. As far as meeting the needs of families with young children is concerned, we have that covered too! In addition to the highchair/booster seat, we provide a gate for the stairs, a Pack-N-Play, and a kiddie pool. We have even secured the 2 chests of drawers in the bedrooms to the walls for the little ones' safety and both TVs are also secured to prevent tip over and possible injury. Young or old, the side road and bike trails that run along the main street provide a safer cycling experience than riding in with the traffic. We also look forward to your return.
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Orlando, Florida USA

It felt like home the minute we walked in and looked forward to returning too at the end of the day.

  • 5 of 5

The Windley Cottage and Anglers Reef exceeded our expectations. Both were top notch and you don't even have to leave the property to enjoy the Keys. The community is quaint and cozy and the house is warm and cozy with just enough of that island feel. The cottage had everything you could need to feel right at home and the bikes and kayakes were a great addition to the amenities. The beaches and the pool were pristine and the boat slips were super nice. We will definitely be bringing our boat next time. Everyone who has seen our pictures of the place thought it was amazing. It definately made our first trip to the Keys amazing and we will definately be back at least once a year. Thanks for sharing your "little slice of heaven" with us and making sure our daughter had a sweet sixteen birthday to remember and a great first trip to Islamorada for the rest off us.

  • Review Submitted: 25-Mar-2018
  • Date of Stay: March 2018
  • Source: HomeAway
Owner's Response: A warm and cozy "slice of heaven" is precisely what our future vacationers will love about our home too! We're glad you enjoyed our complimentary bikes and kayaks and that your daughter had a wonderful and memorable sweet sixteen birthday vacation. We're thrilled to be part of that one time memory! Please allow us to share a picture or two of this, your first trip to the Keys so that our future guests can get a glimpse of what awaits them at Windley Cottage!
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Beautiful and Clean!!

  • 5 of 5

Linda and Roger could not have been more attentive hosts. The house was lovely and the cleanest place we have ever stayed on Home Away. The only minor glitch was an issue with the dishwasher which I hear was being resolved the day we left.

  • Review Submitted: 17-Mar-2018
  • Date of Stay: March 2018
  • Source: HomeAway
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Beautiful, clean and comfortable home - we had the best week!

  • 5 of 5

This was our first stay at Angler’s Reef and it did not disappoint! The whole property is gorgeous and the kids loved the pool, fishing off the beach and kayaking out to the sandbar. The home had everything we needed and is a quick drive or bike ride to many amazing restaurants. We can’t wait to come back!

  • Review Submitted: 17-Mar-2018
  • Date of Stay: March 2018
  • Source: HomeAway
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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)

FL Keys Water Sports

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

Lorelei Cabana Bar


Islamorada Shrimp Shack

Whale Harbor Seafood Buffet

Island Grill

Hog Heaven

Green Turtle Inn

Smugglers' Cove

Midway Cafe

Mango Mike's

Midway Cafe

Bob's Bunz

Bad Boy Burritos II

Mrs. Mac's Kitchen

... and many more!


Prices & Availability

Prices for this holiday house in Islamorada, Florida Keys

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
7 Apr 2018 - 31 May 2018
7 night minimum stay
for 7 nights
1 Jun 2018 - 20 Jul 2018
7 night minimum stay
for 7 nights
21 Jul 2018 - 27 Jul 2018
7 night minimum stay
for 7 nights
28 Jul 2018 - 10 Aug 2018
7 night minimum stay
for 7 nights
11 Aug 2018 - 24 Aug 2018
7 night minimum stay
for 7 nights
25 Aug 2018 - 16 Nov 2018
7 night minimum stay
for 7 nights
17 Nov 2018 - 23 Nov 2018
7 night minimum stay
for 7 nights
24 Nov 2018 - 21 Dec 2018
7 night minimum stay
for 7 nights
22 Dec 2018 - 4 Jan 2019
7 night minimum stay
for 7 nights
5 Jan 2019 - 5 Apr 2019
7 night minimum stay
for 7 nights
6 Apr 2019 - 31 May 2019
7 night minimum stay
for 7 nights
1 Jun 2019 - 19 Jul 2019
7 night minimum stay
for 7 nights
20 Jul 2019 - 26 Jul 2019
7 night minimum stay
for 7 nights
27 Jul 2019 - 31 Aug 2019
7 night minimum stay
for 7 nights
1 Sep 2019 - 15 Nov 2019
7 night minimum stay
for 7 nights
My Standard Rate
7 night minimum stay
for 7 nights

Additional pricing information

Exit Cleaning fee (+Tax) £118.07 + Tax
Property Damage Protection £43.81


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, HomeAway.com 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 for cancellations more than 60 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Ask Owner a Question