"Windley Cottage" is a spotless 2/2.5 Islamorada home located at mile marker 85, away from the highway. Gated, with gorgeous pool and private beach from which to launch our kayaks and paddle boards. Whether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer!
For a laidback vacation, take a leisurely stroll among the “Bahamian conch style" homes tucked in among lush landscaping. Lounge pool-side with a good book. At sunset, relax with your favorite beverage on our private beach. Then dine at one of the fabulous nearby restaurants, many offering nightly entertainment.
Visit some of the local artist's shops, Robbie's gift shop, or the Rain Barrel. Explore the Windley Key State Geological Site, a former coral rock quarry, where fossils of sea creatures can be seen throughout the park. For a bit more history, stop by the 1935 Hurricane Memorial. Angler's Reef is centrally located and perfect for exploring all of the Florida Keys! For a day trip, head down Route 1, over the Seven-mile Bridge to Key West and the Southernmost Point in the US.
If you're looking for an adventure packed vacation, start your day with a few laps of our temperature-controlled pool, mere steps from the house. Then paddle out to the sandbar on our complimentary paddle boards or kayaks. After lunch, 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 by boat from Angler's Reef. 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 in the great room and turn on the fireplace as you cuddle up to watch your favorite movie after a busy day.
For a fee, dock your boat in our protected lagoon with direct, deep-channel access on the Atlantic. No Boat? Rent a boat or jet skis from one for the local marinas. Book a fishing, scuba, snorkeling charter or party boat at Robbie's. Fishing is a must, since Islamorada is known as the "Sport Fishing Capital of the World". Whether flats-fishing in the back bays, deep-water fishing for big game, or fishing from our docks, you're sure to have a great experience. Swim with the dolphins and learn about the local marine life at Theater of the Sea (1/2 mile from our home).
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, 3 paddle ball courts, bocce, tennis, a large playground, basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park.
Other municipal parks include the Islamorada Library Beach and Anne’s Beach.
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!
We offer flexible bed arrangements to meet your group's needs. Call 239-250-4135 for more information.
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 of this property.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Mariners Club 114, VRNR Luxury Collection, Epic Amenities, Indoor Pickleball
Rock Harbor
Mariners Club 114, VRNR Luxury Collection, Epic Amenities, Indoor Pickleball
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
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. Consider Hog Heaven for a night out or MoradaWay Arts & Cultural District if you're travelling with kids. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.
Windley Key Fossil Reef Geological State Park - 7 min walk - 0.7 km
Theater of the Sea - 10 min walk - 0.9 km
Robbie’s of Islamorada - 13 min drive - 16.0 km
Anne's Beach - 19 min drive - 23.9 km
Getting around
Miami International Airport (MIA) - 101 min drive
Restaurants
Wahoo's Bar & Grill - 2 min drive
Hog Heaven - 6 min walk
Starbucks - 18 min walk
Tiki Bar - 2 min drive
The Oceanview Inn & Sports Pub - 11 min walk
Frequently asked questions
Does OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach?
As of 2 July 2026, prices found for a 1-night stay for 2 adults at OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach on 12 Sept 2026 start from AU$588, 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 OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach pet-friendly?
No, pets are not allowed at this property.
How much is parking at OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach?
On-site parking is available at the property.
What time is check-in at OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach?
Check-in begins at 5:00 PM.
What time is check-out at OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach?
Checkout is at 10:00 AM.
Where is OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach located?
Located in Islamorada, this beachfront holiday home is in the city centre and within a 10-minute walk of Hog Heaven and Windley Key Fossil Reef Geological State Park. Founders Park and Islamorada County Park are also within 2 miles (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We both grew up in Western Massachusetts. For many years, we lived and worked in Naples. Now retired, our permanent residence is in Ave Maria, Florida, where we enjoy playing bocce, swimming, and being active 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!
This was our first vacation rental property. Our other location is on Cape Cod in MA. To learn more about our "Seabury Sands" see the Vrbo listing 3757615.
We accept direct bookings to save our vacationers the Vrbo Service Fee.
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
Premier Host
They consistently provide great experiences for their guests