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

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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, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • On beach
  • Heated pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Rooms & beds

2 bedrooms (sleeps 6)

Guest Bedroom

2 Single Beds

Master Bedroom

1 King Bed

Sleeper sofa

1 Queen Sofa Bed

2 bathrooms, 1 half bathroom

Guest Bathroom

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

Half bath on first floor

Soap · Towels provided · Toilet

Master Bathroom

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

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

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

"Windley Cottage" is a private home in the exclusive gated community of Angler's Reef. 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 or simply click on "Book Now". 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.

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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

Check-out instructions

The host requires you to complete the following before checking out:

Start the dishwasher

Strip any used beds and gather used towels

Remove personal items

Turn off the lights and lock the doors

Failure to complete these may result in a negative review from the host.

Upon arrival, if something is broken, notify us immediately so you won't be accountable. If something breaks during your stay, call us 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

Property Registration Number Islamorada Vacation License # 26-0163.
Property # 3970025
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

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. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and hiking/biking trails.
View more Holiday homes in IslamoradaOpens in a new window
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 - 4 min drive - 4.0 km
  • Bud n' Mary's Dive Center - 9 min drive - 11.0 km
  • Baker's Cay Resort Beach - 19 min drive - 24.9 km

Getting around

  • Miami International Airport (MIA) - 101 min drive

Restaurants

  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Hog Heaven - ‬6 min walk
  • ‪Wendy's - ‬5 min drive
  • ‪Starbucks - ‬18 min walk
  • ‪Tiki Bar - ‬2 min drive

Frequently asked questions

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

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

How much does it cost to stay at ISLAMORADA PARADISE in ANGLERS REEF - Pool, Dock, Beach, Kayaks, Paddle Boards?

As of 18 May 2026, prices found for a 1-night stay for 2 adults at ISLAMORADA PARADISE in ANGLERS REEF - Pool, Dock, Beach, Kayaks, Paddle Boards on 12 Sept 2026 start from AU$602, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

No, pets are not allowed at this property.

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

On-site parking is available at the property.

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

Check-in begins at 5:00 PM.

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

Checkout is at 10:00 AM.

Where is ISLAMORADA PARADISE in ANGLERS REEF - 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. 183 out of 192 reviews
Rating 8 - Good. 8 out of 192 reviews
Rating 6 - Okay. 0 out of 192 reviews
Rating 4 - Poor. 0 out of 192 reviews
Rating 2 - Terrible. 1 out of 192 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Kat A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay here! Our kids loved the big pool, the views were beautiful, these cottages are very cute and plenty of room. Definitely perfect for renting a boat. We will definitely come back!!
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Emmy I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great time
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Melissa K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Community was clean and well kept, home was also clean and welcoming.
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Beth H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 14 nights in Jan 2026
Verified

10/10 Excellent

Kenneth A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location was perfect. The house was in perfect shape and well maintained. Just a short 30 second walk to the pool looking out over the Atlantic. Another 30 second walk to the private beach. Numerous wonderful restaurants on the water within a 10 minute drive. It was a 10 out of 10.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Shannon L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Rene D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Nov 2025
Response from VrboOwner on 10 Dec 2025
Rene, We're pleased you enjoyed your stay in Windley Cottage. Our home is in "Oceanfront Anglers Reef", less than 50 yards from the ocean. Yes, there's one home between us and the ocean and we have peek-a-boo ocean views, which we accurately explain in the listing description and aerial photos. We're sorry that it did not meet your expectations. Second row allows for a quieter stay with less pool noise. Linda and Roger
Verified

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
Verified

10/10 Excellent

Kent W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Lisa F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Kenneth C.

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

An amazing time in Islamorada!

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.
Stayed 7 nights in Mar 2025
Verified

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
Verified

10/10 Excellent

Dean B.

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

Great Visit & Location

We had a wonderful time at Anglers Reef. Highly recommend this rental, the ease of use and location are fantastic!
Stayed 7 nights in Apr 2024
Verified

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
Verified

10/10 Excellent

Phil T.

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

Great place to stay

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.
Stayed 7 nights in Nov 2024
Verified

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
Verified

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
Verified

10/10 Excellent

Leslie G.

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

Week trip to Islamorada

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!!
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

kent n.

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

Fabulous Cottage!

Nicest property we have stayed in so far in the wonderful Angler’s Reef community!
Stayed 7 nights in Apr 2021
Response from VrboOwner on 11 Apr 2021
Kent and Bill, It's fabulous to hear that! We look forward to your return the same time next year! Linda and Roger
Verified

10/10 Excellent

Roger W.

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

Great place

Very nice
Stayed 7 nights in May 2024
Verified

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
Verified

10/10 Excellent

Amy V.

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

Great spring break getaway

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.
Stayed 7 nights in Mar 2025
Verified

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
Verified

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
Verified

10/10 Excellent

Jeffrey L.

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

Beautiful Islamorada Cottage

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.
Stayed 7 nights in Nov 2024

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:

English

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