The Lightkeeper | Old Town Key West Monthly Rental with Parking & Widow’s Walk

A Nautical Home on United Street

Where Every Direction Points to the Water

Set behind a gate on United Street, in the heart of Key West’s Old Town, The Lightkeeper is a private home full of character—designed for guests who want to settle in and enjoy the easy indoor-outdoor rhythm of a longer island stay.

The home takes its name from the working lighthouse lamp mounted on the staircase banister—a small beam that actually turns—and from Key West’s long history as a lighthouse island guiding travelers home. Inside, the details keep going: sea-life art, coral, octopus motifs, and stained-glass compass windows that catch the afternoon light.

More than a place to sleep, the property unfolds as a collection of connected spaces—rooms to gather, corners to retreat to, and a widow’s walk to end the day—creating a natural flow for extended island living.

The Home

Vaulted Ceilings, French Doors, and Room to Breathe

The Lightkeeper reflects the character of historic Key West architecture, with white plank ceilings, French doors throughout, and a layout built for airflow and connection to the outdoors.

The main living space is bright and relaxed, anchored by vaulted wood ceilings, a comfortable sectional, and striking blue arched French doors that open the room to the gardens beyond. Coastal art, nautical accents, and a “Key West” sign give the space a sense of place that feels collected rather than staged.

The kitchen is fully equipped and beautifully finished, with wood cabinetry, stone countertops, stainless appliances, and its own vaulted plank ceiling—ready for everything from a quick island breakfast to a long dinner with the whole group. Adjacent dining seating keeps cooks and guests together.

Each bedroom is designed as its own retreat, most with en-suite baths, giving guests both privacy and independence within the larger home.

Details You Won’t Find Anywhere Else

Working Antiques and Handmade Mechanics

What sets The Lightkeeper apart isn’t just the decor—it’s the details that actually work:

• A working lighthouse lamp on the staircase banister that genuinely spins, casting a slow, turning beam—a nod to Key West’s lighthouse past and the single most memorable thing guests mention.
• Artful, sculptural ceiling fans in the living area—two of them mechanically driven by leather belts running from a single central mechanism, a rare piece of craftsmanship you’ll want to watch in motion.
• Stained-glass compass-rose windows, green-marble showers, and a freestanding outdoor soaking tub that make the everyday feel like part of the experience.

Outdoor Living, Pool & Widow’s Walk

The Widow’s Walk & a Tropical Pool Setting

Set among wood decking, palms, and layered tropical greenery is a resort-style pool, shared with three neighboring homes—a laid back spot to cool off through the warm island afternoons.

Crowning the home is a widow’s walk—the railed rooftop lookout that became a signature of Key West’s grand maritime homes.

In the island’s 19th-century wrecking era—when salvaging cargo from ships that foundered on the reef made Key West one of the wealthiest towns in America—these platforms were where wreckers and their families scanned the horizon for sails and the cry of “Wreck ashore!” The name carries the quieter story too: the wives who climbed up to watch for husbands the sea sometimes never sent home. This is a newer home, and its widow’s walk is a deliberate nod to that heritage—a way to honor the island’s seafaring past, minus the worry.

Today it’s simply the best view on the property. Climb the spiral staircase for open-air views over the treetops and rooftops of Old Town, catch the trade-wind breeze, and watch the light go long over the island. Shaded seating and covered porches give everyone a quiet corner below.

Neighborhood – Old Town / Casa Marina

Quiet, Central, and Close to the Beach

The Lightkeeper sits on United Street, one of Key West’s classic residential streets, on the border of the Heart of Old Town and the Casa Marina districts—an easy base that stays quiet at night while keeping the whole island within reach.

Known for palm-lined streets and historic homes, this part of Key West offers a calmer, more local setting while still being only a short bike ride from the beaches, Old Town, and the island’s main attractions—the closest of which include:

• Higgs Beach
• The White Street Pier
• The West Martello Tower
• El Siboney
• Salute! on the Beach
• Louie’s Backyard
• Parks, tennis courts, and waterfront paths

Duval Street and the Historic Seaport are just a short ride away, making it easy to move between quiet mornings, beach afternoons, and evenings out.

The Accommodations

Below Deck and Up the Riggings: Rooms Across Three Stories

First Floor:

• Living Area: Convenient ½ Bathroom
• Outdoor bathroom with freestanding bath tub

 Second Floor:

• Bedroom 1: King bed, en-suite  full bathroom
• Bedroom 2: King bed, en-suite full bathroom

Third Floor:

The Crow’s Nest

• Bedroom 3: Twin Trundle Beds, 1/2 bathroom

A word on the Crow’s Nest–because it’s part of the charm: it’s the most tucked-away spot in the house, and it takes a little effort to reach. The spiral staircase up to is steep, narrow, and it doesn’t begin until the second-floor porch—accessed either by the home’s exterior elevator or through a second-floor bedroom.

The half bath at the top has cozy, duck-your-head ceilings. All of which makes it less of a standard guest room and more of a private perch: a quiet home office or workspace during a longer stay, or exactly the kind of out-of-the-way den the teenage cousins will call dibs on the moment the family arrives.

PARKING: One off-street parking space.

Good to Know

• Available for monthly stays
• Private, gated home
• Shared pool (with three neighboring units)
  • Heated during winter months
• Private widow’s walk (rooftop lookout)
• Exterior elevator to the second-floor porch
• Ideal for group stays, family travel, and remote work
• Located on a quiet Old Town residential street

Restrictions

• Smoke-free house
• Pets allowed with prior approval. Please contact us.
• No loud parties
• We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.