10/10 Excellent
Kenneth C.
23 Mar 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
An amazing time in Islamorada!
Kenneth C.
Stayed 7 nights in Mar 2025
Entire home
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
Photo gallery for OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
Reviews
10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 6
Popular amenities
Explore the area
Islamorada, FL
- Windley Key Fossil Reef Geological State Park7 min walk
- Theater of the Sea10 min walk
- Founders Park3 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Guest Bedroom
2 Single Beds
Master Bedroom
1 King Bed
Sleeper sofa
1 Double Futon
2 bathrooms, 1 half bathroom
Guest Bathroom
Soap · Towels provided · Toilet · Shower only · Hair dryer
Half bath on first floor
Soap · Towels provided · Toilet
Master Bathroom
Soap · Towels provided · Toilet · Shower only · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area
About this property
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- 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.
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 manager
Roger and Linda Robitaille
Premier Host
Languages
English
Add dates for prices
Amenities
Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
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House Rules
Check in after 5:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Very child-friendly! (See amenities)
Events
No events allowed
Pets
No pets 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
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
Property Registration Number Islamorada Vacation License # VR-058, D.B.P.R. State Vacation Rental License DWE5403337., Islamorada Vacation License # 24-0163.
We should mention
A car is required for transport to and from this property
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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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 - 3 min drive - 2.9 km
- Islamorada County Park - 3 min drive - 3.1 km
- Florida Keys Brewing Co. - 6 min drive - 6.0 km
Getting around
Restaurants
- Lorelei Restaurant & Cabana Bar - 5 min drive
- Hog Heaven - 6 min walk
- Wahoo's Bar & Grill - 2 min drive
- Whale Harbor Restaurant Marina - 3 min drive
- Islamorada Beer Company - 4 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Amy V.
29 Mar 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spring break getaway
Amy V.
Stayed 7 nights in Mar 2025
10/10 Excellent
Michelle H.
5 Apr 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Week in Paradise!
Michelle H.
Stayed 7 nights in Mar 2025
10/10 Excellent
Leslie G.
23 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Week trip to Islamorada
Leslie G.
Stayed 7 nights in Feb 2025
10/10 Excellent
Michael W.
2 Mar 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great time at Anglers Reef
Michael W.
Stayed 7 nights in Feb 2025
10/10 Excellent
Sue M.
15 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house and area
Sue M.
Stayed 7 nights in Feb 2025
10/10 Excellent
Diane P.
28 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property
Diane P.
Stayed 7 nights in Jan 2025
10/10 Excellent
Maria C.
2 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely architecture!
Maria C.
Stayed 7 nights in Jan 2025
10/10 Excellent
Kathy R.
15 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely Condo in a Welcoming Neighborhood
Kathy R.
Stayed 7 nights in Feb 2025
10/10 Excellent
Phil T.
22 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay
Phil T.
Stayed 7 nights in Nov 2024
10/10 Excellent
Jeffrey L.
25 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Islamorada Cottage
Jeffrey L.
Stayed 7 nights in Nov 2024
10/10 Excellent
Dean B.
15 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Visit & Location
Dean B.
Stayed 7 nights in Apr 2024
10/10 Excellent
Roger W.
2 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place
Roger W.
Stayed 7 nights in May 2024
10/10 Excellent
Anita O.
1 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
The best week in Islamorada
Anita O.
Stayed 7 nights in Jun 2024
10/10 Excellent
WILLIAM H.
6 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Retired
WILLIAM H.
Stayed 7 nights in Apr 2024
10/10 Excellent
Robyn O.
28 Dec 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stay 12/16-23
Robyn O.
Stayed 7 nights in Dec 2023
10/10 Excellent
James P.
17 Sept 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
I was overwhelmed with the place we stayed at it was beautiful location!
James P.
Stayed 7 nights in Sep 2023
10/10 Excellent
kent n.
11 Apr 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Cottage!
kent n.
Stayed 7 nights in Apr 2021
10/10 Excellent
Heather R.
5 Mar 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful house and hosts
Heather R.
Stayed 7 nights in Feb 2024
10/10 Excellent
Natali T.
1 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Fall Break
Natali T.
Stayed 7 nights in Sep 2023
10/10 Excellent
Verified traveller
16 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Property
Verified traveller
Stayed 10 nights in Oct 2023
10/10 Excellent
Tana M.
11 Feb 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
1st
Tana M.
Stayed 7 nights in Jan 2024
10/10 Excellent
Patrick M.
25 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Home
Patrick M.
Stayed 7 nights in Apr 2023
10/10 Excellent
William D., Montville, NJ
16 Dec 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great FL Keys Location by the Sea
William D.
Stayed 7 nights in Dec 2023
10/10 Excellent
Greg B.
1 Jan 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Islamorada get away
Greg B.
Stayed 7 nights in Dec 2022
About the host
Hosted by Roger and Linda Robitaille
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!
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
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