OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach | House in Islamorada

10.0 (193 Reviews) |   3 Bedrooms  2 Bathrooms  6 Guests
Islamorada House | OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach

3 Bedroom House in Islamorada

"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.

OCEANSIDE ANGLERS REEF 2/25 HOME- Gated community- Pool, Dock, Private Beach is located in Islamorada. OCEANSIDE ANGLERS REEF 2/25 HOME- Gated community- Pool, Dock, Private Beach provides accommodation, featuring View, Balcony/Terrace, Bedding/Linens, among other amenities. This House features View, Balcony/Terrace, Bedding/Linens, to make your stay a comfortable one.

OCEANSIDE ANGLERS REEF 2/25 HOME- Gated community- Pool, Dock, Private Beach has 3 Bedrooms , 2 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Islamorada has interesting places to visit. If you want to learn more about the House in Islamorada, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pool
TV
View
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Eco Friendly
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

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
Child Policy
Children are welcome. note from host: very child-friendly! (see amenities)
Pet Policy
Pets not allowed

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number islamorada vacation license # 26-0163. property registration number islamorada vacation license # vr-058, d.b.p.r. state vacation rental license dwe5403337, islamorada vacation license # 24-0163. safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

License number: Islamorada Vacation License # 26-0163.

Reviews

Beth H.
Jan 27, 2026 06:32:01 AM
Review Score:   10
Summary: 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.
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FAQ's

Is this Islamorada house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Islamorada house have a swimming pool?

Yes, this Islamorada house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Islamorada house?

Best-rates for the Islamorada house starts from $432 per night with includes Pool, TV, Fireplace/Heating, Internet, Laundry, Air Conditioner, Ocean View, Oceanfront, Security/Safety, Wellness Facilities, Parking, Sports/Activities, Entertainment, View, Balcony/Terrace, Bedding/Linens, Eco Friendly, Barbecue/Outdoor Cooking, Child Friendly, Kitchen with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Islamorada house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Islamorada house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Islamorada house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Islamorada house?

Based on the information reported by the owner or manager, the Islamorada house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Islamorada house?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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