Coastal
·Florida Keys, Florida
·Now Booking
Waypoint
A four-bedroom canal-front residence with a private pool and dockage in Islamorada's Venetian Shores.
Overview
Waypoint sits in Venetian Shores, Islamorada's premier waterfront neighborhood on Plantation Key — a canal-front residence with dockage, a private pool, and open water a short idle away in the sport fishing capital of the world.
Four bedrooms and four baths sleep eight. An open main level pairs a modern kitchen and generous island with living space that opens to water views, while the lower level adds flexible living and a bonus room that leads straight out to the pool deck.
Architecture
Grounded in place.
Classic Keys coastal architecture in white board-and-batten and standing-seam metal, with wrapping verandas, louvered shutters, and shaded balconies on both levels.
Interior Design
Warm. Restrained. Considered.
Bright, open, and unfussy — pale wood, coastal blues, crisp millwork, and high-end appliances in a kitchen built for entertaining. Comfortable rather than precious, and made for wet feet after a day on the water.
Gallery
Inside the residence.
Photographed on site. What you see is what you stay in.
Amenities
Every detail, attended to.
Outdoor Activities
A calendar written by the outdoors.
01
Blue-water sport fishing
Sailfish, marlin, mahi and tuna within a short run through Alligator Reef and the Gulf Stream.
02
Flats & backcountry angling
Bonefish, tarpon and permit on the fabled Islamorada flats with a private guide.
03
Snorkeling & diving
The only living coral barrier reef in the continental United States, minutes from the dock.
04
Paddleboarding & kayaking
Mangrove creeks and protected bay water for morning explorations.
05
Waterfront dining
Historic fish houses, oceanfront restaurants, and legendary sunset bars.
06
Sunset cruises
The Keys tradition, on your own vessel or a private charter.
Nearby Attractions
Within an hour's drive.
Islamorada Village
Galleries, chef-driven restaurants, and one of the world's most storied fishing communities.
Bahia Honda State Park
Palm-fringed beaches and clear-water snorkeling under an hour south.
Key West
The southernmost city — historic architecture, Hemingway country, and the sunset ritual at Mallory Square.
Details
Frequently asked.
How many guests does Waypoint accommodate?
Eight guests across four bedrooms — three with king beds and a fourth with two single beds — and four full baths.
Is there dockage for a boat?
Yes. The home sits on a canal with dockage; charter and captain services can be arranged through Legacy.
What is the best time of year to visit?
November through May offers pristine weather; sailfish and tarpon seasons peak in winter and spring respectively.
Inquire
Begin your stay at Waypoint.
Availability is limited and considered on an introductory basis. We invite the conversation.
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