OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
House in Islamorada, FL
6 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceOne of the higher cost properties in the area
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
About this house rental
"Windley Cottage" is a private home in the small 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. Whether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer! Its central location is perfect for exploring all of the Florida Keys!
We have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our 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. Fish or 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! Play pickle ball, tennis, swing, or swim at nearby Founders' Park. 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, 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 more information.
We have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our 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. Fish or 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! Play pickle ball, tennis, swing, or swim at nearby Founders' Park. 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, 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 more information.
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Gym or Fitness Center
Garden
Family friendly
Map of Islamorada, FL
££££
Ratings and reviews
Summary of reviews
Guests consistently praised the property for its cleanliness, beautiful design, well-equipped amenities, and the security of the gated community. They appreciated the easy access to water activities, pool, and nearby attractions, making it an ideal location for families.
10.0 / 10.0
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.
10.0 / 10.0
Very nice
10.0 / 10.0
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.
10.0 / 10.0
We had a wonderful time at Anglers Reef. Highly recommend this rental, the ease of use and location are fantastic!
10.0 / 10.0
This house is beautiful, updated, and so clean! I really cannot overstate that. We travel a lot with our boys, and I typically don’t mind much, but always hope the location is clean. It was spotless when we arrived. The house has high ceilings and tons of space, convenient laundry set-up, and I think we counted, like 30 steps from the large pool. It’s in an enclosed neighborhood, and my younger two ran around with other kids playing manhunt at night. With the privacy fence around the houses, we felt they were very safe. Access to paddle boards and kayaks, this place is perfect for families. Our hosts provided tons of local knowledge, contacts, and things to do. It’s close to marinas, restaurants, ice cream. Loved it!!
8.0 / 10.0
Great location in the keys, one of the more upscale gated communities in the keys. Nice pool area, plenty of water activities included. Two private beach areas. (HOA needs to add sand). House was nice, clean and had a very easy Bluetooth app that locked and unlocked the doors. Great idea when you are at the pool or on the water not dealing with keys. Overall experience of the community was great. We went with 2 other families that rented in the same community they did not have to pay to use a boat dock. We put $350 down and ended up not getting a boat we let the owners know a week before and we couldn’t get our money back. I checked the boat dock space while we were on property and it stayed empty all week. Felt like the right thing to do was give us our money back , especially after finding out the others didn’t get charged to begin with. Also, as mentioned above the house was great ,the area was great but the master bedroom mattress was terrible. They need to buy a new mattress. It was very uncomfortable, no comfort left in it at all. Either very cheap mattress or old mattress. We added as many blankets on top of it as possible to try and help. Another item to note is the garbage pick up comes twice on a Saturday to Saturday stay. Impossible to sleep past 445am. Woke everybody in our house up each time, as well as the other two families staying in anglers. Overall stay was great except the mattress. Would recommend if they put a new mattress on the bed.
10.0 / 10.0
Beautiful house in a nice gated community with a warm, clean pool overlooking the ocean. The complex includes a private beach and marina, and the house is within walking distance of a few restaurants and Theater of the Sea. Roger and Linda were very accommodating hosts and provided clear and helpful communications at every step. I really enjoyed my stay and would love to come back here again!
10.0 / 10.0
It was our first time to the keys.....the stay made us feel very comfortable...safe....and special to be able to have this opportunity.....thank you.
10.0 / 10.0
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.
10.0 / 10.0
This is a great location with amazing amenities; the place had a ton of staples plus bikes, kayaks, etc. The hosts were very communicative and on top of everything. When we had hiccups, they quickly solved them. Note that if you like to turn off the AC and have all the windows open, you can't do that in this unit.
10.0 / 10.0
Had a great stay at anglers reef.
House and property were wonderful.
We enjoyed the kayaks and fishing from the dock.
10.0 / 10.0
Great FL Keys Location by the Sea. Home was great and as advertised. Loved the proximity to everything in Islamorada and the amenities of the Anglers Reef community.
The use of the bikes, kayaks and paddleboards is a nice plus. Fishing options galore are everywhere - on shore, under bridges at inlets or shore boat excursions.
10.0 / 10.0
Very calming, cozy decor. Accommodations great. Had everything we needed. Nice supply of kitchen appliances and gadgets. Perfect location. Close to entrance. Steps from pool. Quiet atmosphere. Pool was beautiful. Easy access of bikes and kayaks. Grocery store and many restaurants close by. Definitely considering coming back.
10.0 / 10.0
This is the second time we rented Windly Cottage and would stay again.
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
This home was just perfect for a friends vacation! There was plenty of room, a great fully stocked kitchen, a back porch to eat breakfast or a late nite cocktail! The neighborhood is beautiful, the landscaping and up lighting is gorgeous, but the pool was the place to be ! We took advantage of the kayaks and paddled out to the sandbar !!! The location couldn’t have been better, every restaurant was amazing, but our favorite by far was Morada Bay beach cafe, tables spread out on sand with an unbelievable sunset, great drinks and an affordable menu!!! We watched the sunset there one nite then went across the street back to the house and watched the full moon rise over the gulf from the beach there !!! Where else can u do that !!!! Unbelievable!!!! We are big “Bloodlines” fans and used the coffee table book to check out sites from the show 💕 we also took the Clear kayaking tour, it goes through the tunnels in the mangroves … so much fun ! We made so many memories with our friends !!!! I miss it already!!!!
10.0 / 10.0
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!
10.0 / 10.0
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…
10.0 / 10.0
The grounds are beautiful, well kept. the pool was clean and the area around the pool organized. The cottage is gorgeous! Linda and Roger are wonderful hosts, made sure our check-in was easy, provided us with all the info about the property and the house. gave us extra recommendations on restaurants and things to do in the area. the house was clean, well supplied with dishes and towels. we felt taken care off. We definitely would love to come back and stay at the cottage again. Thank you, Linda and Roger!
The Suroivcks
10.0 / 10.0
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!
10.0 / 10.0
Very well appointed with two walk-in showers and 1/2 bath downstairs. Easy walk to pool and ocean .
10.0 / 10.0
Great unit in an awesome location everything you need and more! We will be back next year.
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
Clean, inviting, all amenities at hand.
10.0 / 10.0
We had the most wonderful stay in this home. We watched the sunrise each day on the beach and we enjoyed the paddle boards, kayaks and pool. We also enjoyed staying in and cooking the fish we caught. The owners, Linda and Roger, were perfect hosts and responded very quickly to our questions. An A+ vacation in an A+ home. We definitely plan to return.
10.0 / 10.0
I can’t say enough about how perfect Windley Cottage is for vacation. The house is pristine yet comfortable. Best equipped kitchen of any rental we’ve stayed in, and other amenities like bikes, beach chairs, umbrella and beach towels! Spacious and perfect for our family of 4 (2 beds, 2.5 baths, large open living room/kitchen area). Board games and books for elementary aged children gave our kjds variety.
The community is adorable, the pool is steps away, and the beach is a minute walk. Kayaks and paddle boards available for use, or just sit on the beach and look for fish and crabs. We kayaked and fished every day!
There are restaurants and marinas within walking distance, and gorgeous state parks for hiking, swimming and snorkeling within 30 min drive. You can explore all of the Keys in either direction from this perfect location.
The homeowners are very responsive-answered questions within minutes both before and during our stay. They also provided info about local attractions before our trip, so we had time to plan some of our days. We would 100% stay here again!
10.0 / 10.0
Great location. Really enjoyed the key experience with family of 4.
10.0 / 10.0
We had a wonderful vacation at Windley Cottage. It was our first visit to the Keys and it exceeded expectations. The house is very nice and has everything you could need for a week long trip away from home. There were some things in the house that helped reduce what we needed to bring for our two small kids like a pack and play and kids cups.
The pool is great and was never crowded. We spent part of each day there and it was plenty warm for us in November.
We fished right off the community dock and caught a wide variety of fish. I was surprised how many different kinds were there. We saw numerous nurse sharks and barracudas in the water around where the boats are. Kids enjoyed that. A manatee and baby manatee visited the dock area most days as well. A small stingray came to the beach and there were hermit crabs too. So if your kids like ocean animals you’ll be in a good place. Water was calm enough for wading and kayaking.
House is in a great location for restaurants. groceries, etc. the hosts were very nice and responsive. They provided excellent information to help make our stay better. Honestly can’t think of anything negative to say. We would come back again for sure and plan to!
10.0 / 10.0
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
10.0 / 10.0
We just returned form our stay at 129 Angler’s Way, located in Angler’s Reef, Islamorada, Fl.
We had a wonderful time! The property is beautiful and very well maintained! There are
boat docks that provide easy access to the Atlantic
Ocean. It’s just a short ride to an amazing sandbar.
The neighborhood is very friendly! They have a
beautiful community pool. We have stayed in Angler’s Reef many times and keep coming back!
This is the first time we have stayed at 129 Anglers Way… also know as Windley Cottage! The house is beautiful, warm and welcoming!
Pretty colors, beautiful beach decor! The house was very clean! All the appliances were great.
The AC was excellent! The TV was large and had a wonderful picture! The back porch is a perfect place to chill and relax! The owners were great!
They had tons of great information and wonderful communication!
It was perfect! We hope to spend two weeks
In Windley Cottage next summer!
Jennifer & Jeff West
10.0 / 10.0
Perfect location
We loved the convenience on and off the water. Roger and Linda have a great place to enjoy boating, fishing or relaxing on the deck or even at the pool. I would certainly recommend staying here. Can’t wait to return!
10.0 / 10.0
Picture perfect
Everything was perfect…the house, the neighborhood, the location! Best family vacation.
10.0 / 10.0
Perfect location!
I wanted a vacation rental that was in the middle of the Keys. This was an ideal location with a grocery store close by. The men in my group were able to do their bucket list fishing trip and me and my daughter spent time at the beach, pool, and snorkeled frequently. Our day I. key West didn’t disappoint. We had so much fun!
10.0 / 10.0
Wonderful Family Getaway
My wife and I, along with our two children, absolutely loved visiting Islamorada and the Anglers Reef community. Everything about our stay was as good or better than expected. Our hosts, Linda and Roger were very thorough with information regarding the property as well as local getaways and favorite restaurants. The house was perfect for our family of four and the location couldn't be beat. My wife and daughter loved the access to paddle boards and kayaks and my son loved fishing off the community dock. We thoroughly enjoyed our stay!
10.0 / 10.0
Amazing House in Islamorada
We had a wonderful stay! Easily checked in. House was very clean and fully equipped. Owners were extremely responsive. Pool is just steps away and heated to a comfortable temperature. Plenty of poolside chairs and available shade. We were able to take walks in the area and even to restaurants. Islamorada is a convenient location on the Keys.
10.0 / 10.0
2 weeks in Islamorada
Just as advertised, perfect sized home for 4 with amenities included (nice pool, bikes, kayaks and paddle boards). Home was clean and well maintained. Walking distance to 2-3 restaurants /bars and Starbucks. Some pool chairs and kayak equipment could use a bit of sprucing up, but that is an HOA thing. Owners were very responsive whenever we had a question. Islamorada has tons of restaurants and bars, and if you are into fishing, lots of charter boats available for either ocean or bay fishing.
FAQs
How much does this house cost compared to others in Islamorada?
The average price for a rental in Islamorada is £341 per night. This rental is £39 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards. Enjoy the water!
Is OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards?
We found 13 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and fireplace.
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Pool · Kitchen or Kitchenette · Air conditioner
Looking for a Hotel in Islamorada, this Hotel for £336 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
££££
Islander Bayside Villas and Boatslips
Hotel
in Islamorada3-star
2 guests · 2 bedrooms · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner
Experience vacation in Islamorada with our Hotel, Islander Bayside Villas and Boatslips. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
££££
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
House
in Islamorada6 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed
Experience the best of Islamorada with this House available for £349. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
££££
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
Apartment
in Islamorada6 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
This attractive Apartment in Islamorada, £365 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
££££
Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym
Apartment
in Islamorada6 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette
This attractive Apartment in Islamorada, £454 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
££££
WOW!! WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CLEAN-CONTACT OWNER
House
in Islamorada Village of Islands8 guests · 4 bedrooms · 2 baths
Garden · Pool · Pets allowed
Experience vacation in Islamorada with our House, WOW!! WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CLEAN-CONTACT OWNER. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
££££
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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool
House
in Islamorada6 guests · 2 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Islamorada at Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool for £409 for your next trip.
££££
Brand New / Totally Renovated Luxurious Home with POOL
House
in Islamorada8 guests · 3 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Islamorada, at £421 per night for your next great vacation.
££££
Paradise Found - Three Story Beach House w/ private beach, dock and Ocean Views
Villa
in Islamorada6 guests · 3 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Most favorited
Villa in Islamorada, for £426 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
££££
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
House
in Islamorada6 guests · 2 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Islamorada? Look no further than our House, Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
££££