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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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A heated pool
Property grounds
Children's area
Fridge, microwave, oven, stovetop
Marina
In the heart of Islamorada, Windley Cottage offers a tranquil retreat. This tastefully-decorated home is nestled among lush landscaping and just steps from the pool and docks. Enjoy a swim in our temperature-controlled pool or paddle out to the sandbar on our paddle boards or kayaks.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 6

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Gym

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Heated pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Car required
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster
  • Water dispenser

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2.5 private bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Netflix
  • Smart TV with cable/satellite channels
  • Streaming services

Outdoor areas

  • Balcony
  • Barbecue grill
  • Dock
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a village
  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near the marina
  • Near the ocean

Things to do

  • Boat
  • Golf
  • Gym
  • Heated pool
  • Kayak
  • Pickleball
  • Tennis
  • Water park
  • Water sports equipment
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • Comprehensive recycling policy
  • Double-glazed windows
  • Eco-friendly cleaning products used
  • Electric car charging station
  • Energy-saving switches in guestrooms
  • Garden
  • Gated community
  • Local artist showcase
  • Locally-owned and organized tours and activities
  • No plastic coffee stirrers
  • No plastic drinking straws
  • No plastic soft drink bottles
  • No plastic water bottles
  • Property located in a resort
  • Reusable cups
  • Reusable tableware
  • Water dispenser usage encouraged
  • Water-efficient showers
  • Water-efficient toilets

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Policies

Check-in

Check-in time starts at 5:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

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.

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Very child-friendly! (See amenities)

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number Islamorada Vacation License # 24-0163.

We should mention

A car is required for transportation to and from this property

Property is also known as

Anglers Reef Keys Ocean Views Pool Slip Beach Child-friendly
Anglers Reef Keys Ocean Views Pool Slip Beach Fall Special House
Anglers Reef Keys Ocean Views Pool Slip Beach Fall Special
Anglers Reef Islamorada Ocean Views Pool Slip Beach House
Anglers Reef Ocean Views Pool Slip Beach House
Anglers Reef Islamorada Ocean Views Pool Slip Beach
Anglers Reef Islamorada Ocean Views Pool Slip Beach House
Anglers Reef Islamorada Ocean Views Pool Slip Beach
Anglers Reef Ocean Views Pool Slip Beach
Anglers Reef Islamorada Ocean Views Pool Slip Beach House
25 OFF MAY 1-8 Anglers Reef Ocean Views Pool Slip Beach House
Anglers Reef Ocean Views Pool Slip Beach House
25 OFF MAY 1-8 Anglers Reef Ocean Views Pool Slip Beach
Anglers Reef Islamorada Ocean Views Pool Slip Beach
Anglers Reef Ocean Views Pool Slip Beach
Anglers Reef Islamorada Ocean Views Pool Slip Beach

About the neighborhood

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 Intl. 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?

Onsite 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?

Check-out is at 10:00 AM.

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

Located in Islamorada, this beachfront vacation home is in the city center 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 mi (5 km).

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

Reviews

10

Exceptional

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

P H.

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

Great location for family

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.
Stayed 7 nights in May 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

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

Michelle H.

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

A Week in Paradise!

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!
Stayed 7 nights in Mar 2025

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

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

Michael W.

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

Another great time at Anglers Reef

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.
Stayed 7 nights in Feb 2025

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

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

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

10/10 Excellent

Roger W.

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

Great place

Very nice
Stayed 7 nights in May 2024

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

10/10 Excellent

Robyn O.

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

Stay 12/16-23

Had a great stay at anglers reef. House and property were wonderful. We enjoyed the kayaks and fishing from the dock.
Stayed 7 nights in Dec 2023

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

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

Anita O.

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

The best week in Islamorada

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.
Stayed 7 nights in Jun 2024