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OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Family-friendly beachfront location with water park

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129 Anglers Way, Angler's Reef, Islamorada Village of Islands, Florida Keys
Living room
Counter dining
Dining area
Master bedroom

Reviews

10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • Parking available
  • Gym
  • Dryer
  • Washer

Explore the area

View map
Islamorada, FL
  • Place, Windley Key Fossil Reef Geological State Park
    ‪7 min walk‬
  • Place, Theater of the Sea
    ‪10 min walk‬
  • Place, Bud n' Mary's Dive Center
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Guest Bedroom

2 Single Beds

Master Bedroom

1 King Bed

Sleeper sofa

1 Double Futon

2 bathrooms, 1 half bathroom

Guest Bathroom

Soap · Towels provided · Toilet · Shower only · Hair dryer

Half bath on first floor

Soap · Towels provided · Toilet

Master Bathroom

Soap · Towels provided · Toilet · Shower only · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

"Windley Cottage" is a private home in the exclusive gated community of Angler's Reef in Islamorada. This welcoming, tastefully-decorated home is located at mile marker 85, 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. ts central location is 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, 3paddle ball courts, bocce, tennis, a large playground, and basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park. Bring your rental agreement for free entry to the 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 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. When you find the perfect dates for your stay, simply click on "Book Now".

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.

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Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 5:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Very child-friendly! (See amenities)
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Should something break or not operate correctly, notify us immediately so we can fix the problem ASAP.
Boat Slip Rental Fees are non-refundable. No upper station or boats exceeding 9.0 feet bridge clearance are allowed. No sub-letting slip or house.
Apply aerosol sprays outside and away from the decks.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number Islamorada Vacation License # 24-0163.

We should mention

A car is required for transport to and from this property

About the area

Islamorada

Located in Islamorada, this holiday home is in the city centre and on the beach. History of Diving Museum and Keys History & Discovery Center are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Islamorada, FL

What's nearby

  • Windley Key Fossil Reef Geological State Park - 7 min walk - 0.7 km
  • Theater of the Sea - 10 min walk - 0.9 km
  • Founders Park - 5 min drive - 3.7 km
  • Bud n' Mary's Dive Center - 14 min drive - 11.3 km
  • Anne's Beach - 28 min drive - 23.5 km

Getting around

  • Miami International Airport (MIA) - 101 min drive

Restaurants

  • ‪Tiki Bar - ‬2 min drive
  • ‪Hog Heaven - ‬6 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Starbucks - ‬18 min walk
  • ‪Marathon Bagel Co - ‬3 min drive

Frequently asked questions

Does OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards pet-friendly?

No, pets are not allowed at this property.

How much is parking at OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards?

On-site parking is available at the property.

What time is check-in at OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards?

Check-in begins at 5:00 PM.

What time is check-out at OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards?

Checkout is at 10:00 AM.

Where is OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards located?

Located in Islamorada, this beachfront holiday home is in the city centre and within 2 mi (3 km) of Windley Key Fossil Reef Geological State Park, Founders Park and Islamorada County Park. Rain Barrel Village and History of Diving Museum are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 176 out of 185 reviews
Rating 8 - Good. 8 out of 185 reviews
Rating 6 - Okay. 0 out of 185 reviews
Rating 4 - Poor. 0 out of 185 reviews
Rating 2 - Terrible. 1 out of 185 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

Darrell P.

Liked: Cleanliness, communication, location, listing accuracy
Overall a good trip. A few items needed to be taken care of, but it didn't stop us from having a great time.
Stayed 7 nights in Jul 2025

10/10 Excellent

harry s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Keys Stay

Lodgings first rate. Boat access to Mahi and Grouper catches.
Stayed 7 nights in May 2025

10/10 Excellent

Emily C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Islamorada vacation

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!
Stayed 7 nights in Apr 2025

10/10 Excellent

Diane P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property

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!
Stayed 7 nights in Jan 2025

10/10 Excellent

Kim K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

PERFECT STAY

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!
Stayed 7 nights in May 2025

10/10 Excellent

Maria C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely architecture!

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!
Stayed 7 nights in Jan 2025

10/10 Excellent

James P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

I was overwhelmed with the place we stayed at it was beautiful location!

It was the nicest little community I ever saw it was the best . I could keep my boat at the Slip. The place was beautiful. Great location.
Stayed 7 nights in Sep 2023

10/10 Excellent

Sue M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house and area

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.
Stayed 7 nights in Feb 2025

10/10 Excellent

Patrick M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Home

Perfectly equipped, spotlessly clean, very comfortable! Perfect location, the complex is super nice, pool is great and entire complex is extremely well kept. We would definitely stay here again…can’t wait…
Stayed 7 nights in Apr 2023

10/10 Excellent

Greg B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Islamorada get away

Clean, inviting, all amenities at hand.
Stayed 7 nights in Dec 2022

10/10 Excellent

Natali T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Fall Break

We truly enjoyed our stay and found Angler’s Reef to be a wonderful property. Linda and Robert are great hosts, super responsive, and Windley Cottage is beautifully, decorated and exceptionally clean. We will be back for sure!
Stayed 7 nights in Sep 2023

10/10 Excellent

Molly H., Otsego

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for us!

Great unit in an awesome location everything you need and more! We will be back next year.
Stayed 7 nights in Feb 2023

10/10 Excellent

Kathy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Condo in a Welcoming Neighborhood

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!
Stayed 7 nights in Feb 2025

10/10 Excellent

Susan W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely property on Islamorada; inside and out!

Windley Cottage is exactly as advertised. It is clean and comfortable on the inside -- the owners have paid attention to the smallest details of being a guest. We loved being able to use the kayaks! The grounds, pool and beaches at Angler's Reef are beautiful and well-kept. Five enthusiastic stars!

10/10 Excellent

Dave D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Keys vacation

Windley Cottage was a perfect escape from winter for our family. Nice house and community with plenty of amenities. Great pool, kayaks and paddle boards onsite...plenty to do. Tons of restaurants nearby and a good central location to explore all of the Keys. Linda and Roger made the process easy and are very responsive. Highly recommended.
Stayed 7 nights in Dec 2022
This review was submitted before 2018 and has not been verified.

8/10 Good

Greg B.

GREAT PROPERTY FOR FAMILIES

My family of 4 had a great week. The pictures shown are an exact match as to what you get with this property. We saw every type of sea life possible. Direct quote from my kids 5 and 7 " BEST VACATION EVER".
Stayed 7 nights in Jun 2017

10/10 Excellent

WILLIAM H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Retired

Vastly exceeded our expectations in every way, very clean and well laid out cottage, property was beautiful and well maintained, we fely safe and secure while at the property would stay there again.
Stayed 7 nights in Apr 2024

10/10 Excellent

Judith D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise

Anglers Reef is now at the top of our list to return to. The Windley Cottage was home away from home. Equipped with everything we needed. Beautifully decorated, very clean. We loved the pool, paddle boards, and the close proximity to everything. We will return!
Stayed 7 nights in Apr 2023

10/10 Excellent

Kristi H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, Beachy and Comfortable

The Windley Cottage is a lovely home! It was beautifully decorated, comfortably furnished, and it provided a relaxing setting for our week in Islamorada. We enjoyed all of the amenities that were included, such as the kayaks, paddleboards and bikes. The pool area was gorgeous and the ocean view from our chairs was like none other! Roger and Linda were the most helpful and welcoming hosts we have ever rented from. We can't wait to return for another week in paradise!
Stayed 7 nights in Jun 2019

10/10 Excellent

Ralph T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing

Townhome was very clean and updated. Host was very easy to communicate with. Home was well stocked and in a great location for all our needs.Great restaurants nearby. Owners gave detailed list on places to visit and and anything else that would be needed. Would highly recommend this unit in a very well kept and safe development. Thank you
Stayed 7 nights in Aug 2022

10/10 Excellent

Jill M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best family vacation!

We truly loved our stay here! I could tell already from booking that Roger + Linda take pride in their home, and this was one of those rare times that when we arrived, the house was even better than we expected! We found the house to be exceptionally clean and well-stocked. The community is adorable, and we loved the pool, searching for fish on the docks, and taking the kayaks out to the sand bar. We stayed here as a family of four (kids ages 15 + 11) and found it had something for everyone. This was our first trip to the Keys and we had a blast! Thank you, Roger + Linda!
Stayed 7 nights in Apr 2023

10/10 Excellent

JB K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Islamorada Dreamy

The gated community was wonderful. Roger & Linda’s condo is a dream. Everything we needed (and more) was on premise. We had a little trouble with a toilet (normal wear and tear). We gave them a call and within an hour it was fixed. Highly, highly recommend! We will be back!
Stayed 7 nights in Feb 2023

10/10 Excellent

Sharon R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice Stay

Islamorado is our favorite place in the keys. The house we stayed is was great except we ours not get the washer to work. We took only a few clothes so we had to keep washing them in the sink. Other than that it was a great place to stay. Owner kept saying it was the water pressure but other house were able to use their washers.
Stayed 7 nights in Jan 2024

10/10 Excellent

Stephen S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Premier VRBO!

The host was welcoming even before we arrived. They provided a lot of valuable information and we were delighted to know that there would be numerous beach and pool "toys" along with beach towels and bikes. The house was ready before "check in" time which was great. We arrived to find the house spotless and it looked exactly as advertised. The kitchen was well supplied and while we only cooked breakfast, you could easily have made a big dinner. The living area had great seating as did the back porch. The showers are large- the beds are very comfy. We felt very much at home. Whenever we contacted the host, we received a response within minutes and he always followed up. We already plan to stay here again next year.
Stayed 14 nights in Jun 2023

10/10 Excellent

Stuart K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Home in a Excellent location

Highly recommended! We had a great time staying at this property! We have rented many different homes across the US for our vacations over the years and this was by far the cleanest one we have ever rented, it was just spotless. The home is very nicely decorated, well equipped and well maintained, it's located in a very nice small neighborhood that was a great base to explore Islamorada from. We found Anglers Reef to be a very friendly place with beautiful, well kept grounds and a great pool with an amazing view out to sea. The Kayaks and paddle boards that are available for use on the beach were great for paddling out to the nearby sand bars for some snorkeling and swimming. The owners were very friendly and responsive when we had a small issue with the front door lock and supplied a large amount of very helpful information with local restaurant recommendations and things to see and do with the booking confirmation. Overall a great experience and we would definitely stay there again.
Stayed 7 nights in Jun 2023

About the host

Hosted by Roger and Linda Robitaille

Host profile image
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, tropical ocean waters. Now retired, our permanent residence is in Naples, Florida, where we enjoy power-boating, swimming, and bicycling all year long.

Why they chose this property

For years, we dreamed of owning a Keys home. The quaint, well-maintained conch homes and gorgeous landscaping in Anglers Reef captured our hearts immediately! "Windley Cottage" is the perfect location within the community - close to the pool and boat lagoon, yet farther from the road. With its "Keysie" charm and subtle beachy decor, we were sold!

What makes this property unique

Windley Cottage is in an architectural style known as a "Bahamian Conch Cottage" with high ceilings on both floors, porches, balconies, and metal roofing. The community 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).

Our particular home's pastel yellow painted clapboard siding is cheery and inviting. Large double-hung windows allow plenty of light into our home. Sitting on the back porch or on the guest room balcony marveling at the sunrise over the ocean or a sunset to the west is a treat.
The attention to details inside makes our home stand out among the others! It's so much more than a well-outfitted and maintained home! The delightfully decorated interior, includes some bead board and wainscoting, with a few custom beachy accents, complete the home's feel of a luxurious, tranquil accommodation. Mood lighting and an electric fireplace add to the romantic feel. Windley Cottage is truly special and we open our home to vacationers, like yourself, so that you too can enjoy it!

Languages:

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