A Touch of Bermuda in Key West

Note: Minimum stay is 28 nights. Saturday-to-Saturday arrivals and departures required by Homeowner Association rules. No short weekend stays permitted. Pets by special permission.

About This Property
A Touch of Bermuda is a privately owned, two-story Bermuda-style conch cottage in the Shipyard section of Truman Annex — one of only seven private townhomes available for rent in this gated, 24-hour secured community in the heart of Old Town Key West. This is not a condo. Not a managed rental. Not a cookie-cutter vacation unit.

It is a wood-framed cottage with a sloping tin roof, lazily turning overhead fans, a front porch on picturesque Southard Street, and a large private back deck with a dining table for six — the kind of Key West home that defines what a vacation here is supposed to feel like.

The walls are painted in warm, restful colors inspired by the owner's visits to Bermuda. Original Cuban artwork — collected during humanitarian and educational trips to the island — fills the living room, including a painting of the legendary Blue Heaven restaurant. The result is a space with genuine character that no interior designer could manufacture.

This is the owner's personal home. You will feel the difference.

Bedrooms & Privacy
One of this cottage's most valuable features is its two-level bedroom configuration — providing exceptional privacy for two couples or families:

Master bedroom suite — upstairs, with its own private bathroom
Second bedroom and bathroom — downstairs, completely separate
Neither party shares a bathroom — a rare and highly sought-after layout in vacation rentals

Maximum occupancy: 6 guests

Amenities
Technology & Connectivity

High-speed WiFi
Fiber optic TV in both bedrooms (superior to standard cable)

Parking
Free reserved, secure parking behind the cottage — an exceptional and rare amenity in Old Town Key West

Outdoor Spaces
Front porch facing Southard Street — perfect for morning coffee and watching Key West life go by
Large private back deck with comfortable reading chairs and dining table for six — ideal for starlit dinners

Themed Getaway Packages Available:
Honeymoon
Anniversary
Birthday celebration
Week of romance

Contact the owner directly to arrange special touches for your stay.

Frequently Asked Questions

What is the minimum stay?
28 nights, by Homeowner Association rules. Arrivals and departures are Saturday to Saturday. Short weekend stays are not permitted.

Is parking included?
Yes — free reserved, secure parking behind the cottage is included. This is uncommon in Old Town Key West and a significant convenience for month-long stays.

How private is the bedroom layout?
Completely private. The master suite is upstairs with its own bathroom. The second bedroom and bathroom are downstairs. Neither party shares a bathroom — an unusual and highly valued feature.

Is the property good for families with children?
Yes. The Splash Pad water play area is at the end of the street. The heated community pool is steps from the back gate. Fort Zachary Taylor Beach is 800 yards away with full facilities. The Aquarium, Butterfly Expo, and Shipwreck Museum are all within walking distance.

Are water sports accessible?
Yes — snorkeling, scuba diving, and fishing charters all depart from the local pier within walking distance of the cottage.

Is there a pool?
Yes — the heated Truman Annex community pool is steps from the back garden gate via a pebble path.

Are pets allowed?
Pets are welcome by special permission from the owner. Contact directly to discuss.

What TV service is available?
Fiber optic TV in both bedrooms — superior to standard cable in picture quality and reliability. High-speed WiFi is also included.

Can the owner recommend restaurants and local tips?
Absolutely — and enthusiastically. The owner has 25+ years of Key West knowledge and provides a personal recommendations packet at check-in. Ask directly for insider tips that locals don't publish anywhere.

Is there a companion property available?
Yes — the owner also rents a Cuban-inspired casita nearby in the same Truman Annex neighborhood, well suited for smaller parties.

Unique Benefits

One of only 12 private townhomes available for rent in Truman Annex — ever

Gated community with 24-hour security

Free reserved secure parking — rare and valuable in Old Town Key West

Two fully private bedroom suites on separate floors — no shared bathrooms
Fiber optic TV — superior picture and reliability to standard cable

Owner's personal home with original Cuban artwork and Bermuda-inspired design

25+ years of local knowledge shared with every guest

Direct owner communication before and throughout your stay

Companion casita available nearby for smaller parties or additional guests

Why Kids Love It

Splash Pad / Waterfront Park — brand new water play area at the end of the street, perfect for young children
Heated community pool — just steps out the back garden gate down a pebble path
Fort Zachary Taylor Beach — 800 yards away with snack bar, changing rooms, and outdoor showers
Key West Aquarium — short walk
Butterfly Expo — short walk
Shipwreck Museum — short walk
Mel Fisher's Treasure Museum — short walk

Area Information

Truman Annex is a former U.S. Naval base transformed into Key West's premier gated residential community. President Harry S. Truman used the property as his summer White House — the Little White House museum and tours are steps away. The neighborhood is beautifully maintained, 24-hour secured, and positioned midway between the Waterfront Park and Duval Street — the ideal base for exploring everything Key West offers.

Attractions Within Walking Distance

Duval Street — 2 blocks away; Key West's legendary strip of award-winning restaurants, unique shops, art galleries, bars, and nightclubs
Community heated pool — steps from the back garden gate via a pebble path
Fort Zachary Taylor State Park Beach — Key West's best beach, 800 yards away
Mallory Square — famous nightly sunset celebration, short walk
Key West Historic Seaport — snorkel, scuba, and fishing charters within walking distance
Harry S. Truman Little White House — steps away, tours available
Ernest Hemingway Home & Museum — short walk
Key West Aquarium — short walk
Butterfly Expo — short walk
Shipwreck Museum — short walk
Mel Fisher's Treasure Museum — short walk
Southernmost Point — short walk
Waterfront Park & Splash Pad — end of the street
The Cooking Show — Key West's newest attraction, within walking distance

A Short Drive Away:

Key West Golf Club — the only 18-hole public golf course in the Florida Keys, open to the public

Favorite Places To Eat

The owner has personal restaurant recommendations for every taste and budget, collected over 25+ years of Key West life — available in the welcome information packet provided at check-in. Blue Heaven, a Key West institution, is a personal favorite and has been for over two decades. A painting of it hangs in the living room.

Inside Scoop

You have to ask me for tips only locals know so I can get you to make an inquiry about my cottage. The only information I can't share is the winning lottery number.