Hyatt Residence Club Key West, Windward Pointe ★★★★

The Corner of the Island That Faces the Open Sea

Old Town occupies the west end of Key West and takes most of the attention. The southeast corner is a different island: South Roosevelt Boulevard running along the Atlantic, the airport behind it, Smathers Beach stretching away and nothing between the shore and open water. Windward Pointe sits on that corner. The buildings are low and residential, the planting is generous, and the centre of the resort is a free-form infinity pool cut so that its edge disappears into the sea behind it. There is a restaurant at the side of it and hammocks strung where the ocean is in view.

Why It Works

We kept this one for the way it is built. These are villas, not rooms: a full kitchen, a separate living and dining area, a balcony over the water. For a family or for a stay of more than three nights that is a different proposition from a hotel bedroom, and it is why the property fills with people who come back. The Hyatt operation behind it means the standard is predictable across ninety-three units. Parking is free, which on this island is worth stating plainly. And the telescope on the balcony is the kind of detail nobody asks for and everybody uses.

Why This Location

South Roosevelt is the Atlantic side of Key West, and staying here trades the walk to Duval for the view and the beach. Smathers Beach, the longest stretch of sand on the island, starts a few minutes away on foot, and the Southernmost Point is along the same shore. Old Town, Duval Street and the Hemingway Home are a short drive or a bike ride west, and the airport is close enough to make arrival and departure simple. The Overseas Highway runs north from here to Islamorada and Key Largo, so day trips up the chain start at the door.

Fast Facts

• Price: Premium

• Vibe: Residential, oceanfront, family-paced, resort-run

• Rooms: Ninety-three residential-style villas with full kitchens, separate living and dining areas and private balconies with partial ocean views

• Best For: Families, groups, long stays, anyone who wants a kitchen and a living room rather than a bedroom

• Our Favorite Thing About the Hotel: The telescope on the villa balcony, put there for stargazing over the Atlantic and used far more than anyone expects

• Dining: A poolside restaurant on site, communal barbecue grills across the grounds, and a full kitchen in every villa

• Amenities: Free-form infinity-edge pool open all year, hot tub, beach volleyball court, barbecue grills, hammocks facing the ocean, cycling, free parking

• Attractions: Smathers Beach, the Southernmost Point, Old Town and Duval Street, the Ernest Hemingway Home and Museum, Key West International Airport, the Overseas Highway north

Villas Rather Than Rooms

The unit is the point of difference. Each villa comes with a fully equipped kitchen, a living and dining area separate from the sleeping space, and a private balcony with a partial view of the ocean. That layout is what makes a week here work: breakfast without a queue, a cooler packed for the beach, dinner cooked after a long day in the sun, and somewhere for one person to read while another sleeps. The scale is residential rather than corridor-based, and the grounds are planted so the buildings sit among greenery rather than above a car park.

The Infinity Pool and the Grounds

The pool is the piece of design everyone remembers. It is free-form rather than rectangular, cut with an infinity edge that lines up with the horizon so the water appears to run into the Atlantic, and the poolside restaurant sits close enough to make lunch a short walk in bare feet. Around it the resort keeps a hot tub, a beach volleyball court, communal grills and hammocks placed where the ocean is in front of you. Bicycles are the sensible way to reach Old Town. Check-in runs from four in the afternoon to eleven at night, and check-out is at ten.