Cottage in Key West, FL
6 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this cottage rental
Note: Minimum stay is 29 days / 28 nights. Saturday-to-Saturday bookings required. Exceptions made for special events including boat races and Fantasy Fest. Pets by special permission.
About This Property
A Touch of Bermuda is a privately owned 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 cookie-cutter condo. It is a genuine two-story townhome with wood framing, a sloping tin roof, overhead fans, a front porch on picturesque Southard Street, and a large private back deck — the kind of Key West vacation home that is increasingly rare to find.
The warm color palette was inspired by visits to Bermuda, giving the cottage a distinctive, personal character that sets it apart from standard vacation rentals. Cuban artwork on the living room walls reflects the owner's humanitarian and educational travels to the island.
Property Layout & Bedrooms
One of this cottage's standout features is its two-level bedroom configuration, which provides exceptional privacy for two couples or a family:
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 valued layout in vacation rentals
Maximum occupancy: 6 guests
Amenities
Reserved, secure parking behind the cottage (free — an exceptional value in Key West)
High-speed WiFi
Cable TV in both bedrooms
Large back deck with comfortable seating and a dining table for six
Front porch facing Southard Street
Full kitchen
Pets welcome by special permission
Themed Getaway Packages
This cottage is ideal for:
Honeymoons
Anniversary celebrations
Birthday getaways
Romantic escapes
Contact the owner directly to discuss special arrangements.
Special Offer
Book a summer or fall stay and receive a gift certificate to Blue Heaven, a Micheline Guide restaurant!
Location: Truman Annex, Old Town Key West
Truman Annex is a former U.S. Naval base converted into one of Key West's most desirable gated residential communities. President Harry S. Truman used the property as his summer White House — the Little White House museum and tours are steps away. The neighborhood features 24-hour security, lush landscaping, and a community pool, all within easy walking distance of everything Key West is known for.
What's Walkable From This Cottage:
Duval Street — 2 blocks away; Key West's legendary strip of award-winning restaurants, unique shops, art galleries, bars, and nightclubs
Community pool — 100+ steps from the back garden gate via a pebble path
Fort Zachary Taylor State Park Beach — Key West's best beach, within walking distance
Mallory Square — famous nightly sunset celebration, short walk away
Key West Historic Seaport — snorkel, scuba, and fishing charters depart from the local pier within walking distance
Ernest Hemingway Home & Museum — short walk
Key West Aquarium — short walk
Mel Fisher's Treasure Museum — short walk
Splash Pad — family water play area at the end of the street, perfect for young children
Harry S. Truman Little White House — steps away, tours available
A Short Drive Away:
Key West Golf Club — the only 18-hole public golf course in the Florida Keys
Why This Property Stands Out
One of only seven private townhomes for rent in Truman Annex
Gated community with 24-hour security
Free reserved parking — rare and valuable in Old Town Key West
Two fully private bedroom suites on separate floors — no shared bathrooms
Owner's personal home with curated artwork and Bermuda-inspired design
Direct owner communication before and during your stay
A companion casita (VRBO listing #1049465) is available six doors away for smaller parties or overflow guests
Frequently Asked Questions
What makes this different from a typical Key West vacation rental?
This is one of only seven private townhomes available for rent in the gated Truman Annex. It is the owner's personal home — not a managed property — with two fully separate bedroom suites, free parking, and a large private back deck. It offers significantly more space, privacy, and character than a standard condo rental.
Is parking included?
Yes — reserved, secure parking behind the cottage is included at no charge. This is uncommon in Old Town Key West and a meaningful convenience.
How private is the bedroom layout?
Very. The master suite is upstairs with its own bathroom. The second bedroom and bathroom are downstairs. The two sleeping areas are completely separate — neither party shares a bathroom.
Is the property good for families with children?
Yes. The Splash Pad water play area is at the end of the street. Fort Zachary Taylor beach is within walking distance. The community pool is steps from the back gate.
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 Truman Annex community pool is approximately 100 steps from the back garden gate.
What is the minimum stay?
29 days / 28 nights. Bookings typically run Saturday to Saturday. Exceptions are made for special events such as the Key West boat races and Fantasy Fest.
Are pets allowed?
Pets are welcome by special permission from the owner. Contact directly to discuss.
Is there a smaller option available?
Yes — the owner also rents a casita (condo) six doors away in the same Truman Annex neighborhood (VRBO listing #1049465), which is a good option for smaller parties.
About This Property
A Touch of Bermuda is a privately owned 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 cookie-cutter condo. It is a genuine two-story townhome with wood framing, a sloping tin roof, overhead fans, a front porch on picturesque Southard Street, and a large private back deck — the kind of Key West vacation home that is increasingly rare to find.
The warm color palette was inspired by visits to Bermuda, giving the cottage a distinctive, personal character that sets it apart from standard vacation rentals. Cuban artwork on the living room walls reflects the owner's humanitarian and educational travels to the island.
Property Layout & Bedrooms
One of this cottage's standout features is its two-level bedroom configuration, which provides exceptional privacy for two couples or a family:
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 valued layout in vacation rentals
Maximum occupancy: 6 guests
Amenities
Reserved, secure parking behind the cottage (free — an exceptional value in Key West)
High-speed WiFi
Cable TV in both bedrooms
Large back deck with comfortable seating and a dining table for six
Front porch facing Southard Street
Full kitchen
Pets welcome by special permission
Themed Getaway Packages
This cottage is ideal for:
Honeymoons
Anniversary celebrations
Birthday getaways
Romantic escapes
Contact the owner directly to discuss special arrangements.
Special Offer
Book a summer or fall stay and receive a gift certificate to Blue Heaven, a Micheline Guide restaurant!
Location: Truman Annex, Old Town Key West
Truman Annex is a former U.S. Naval base converted into one of Key West's most desirable gated residential communities. President Harry S. Truman used the property as his summer White House — the Little White House museum and tours are steps away. The neighborhood features 24-hour security, lush landscaping, and a community pool, all within easy walking distance of everything Key West is known for.
What's Walkable From This Cottage:
Duval Street — 2 blocks away; Key West's legendary strip of award-winning restaurants, unique shops, art galleries, bars, and nightclubs
Community pool — 100+ steps from the back garden gate via a pebble path
Fort Zachary Taylor State Park Beach — Key West's best beach, within walking distance
Mallory Square — famous nightly sunset celebration, short walk away
Key West Historic Seaport — snorkel, scuba, and fishing charters depart from the local pier within walking distance
Ernest Hemingway Home & Museum — short walk
Key West Aquarium — short walk
Mel Fisher's Treasure Museum — short walk
Splash Pad — family water play area at the end of the street, perfect for young children
Harry S. Truman Little White House — steps away, tours available
A Short Drive Away:
Key West Golf Club — the only 18-hole public golf course in the Florida Keys
Why This Property Stands Out
One of only seven private townhomes for rent in Truman Annex
Gated community with 24-hour security
Free reserved parking — rare and valuable in Old Town Key West
Two fully private bedroom suites on separate floors — no shared bathrooms
Owner's personal home with curated artwork and Bermuda-inspired design
Direct owner communication before and during your stay
A companion casita (VRBO listing #1049465) is available six doors away for smaller parties or overflow guests
Frequently Asked Questions
What makes this different from a typical Key West vacation rental?
This is one of only seven private townhomes available for rent in the gated Truman Annex. It is the owner's personal home — not a managed property — with two fully separate bedroom suites, free parking, and a large private back deck. It offers significantly more space, privacy, and character than a standard condo rental.
Is parking included?
Yes — reserved, secure parking behind the cottage is included at no charge. This is uncommon in Old Town Key West and a meaningful convenience.
How private is the bedroom layout?
Very. The master suite is upstairs with its own bathroom. The second bedroom and bathroom are downstairs. The two sleeping areas are completely separate — neither party shares a bathroom.
Is the property good for families with children?
Yes. The Splash Pad water play area is at the end of the street. Fort Zachary Taylor beach is within walking distance. The community pool is steps from the back gate.
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 Truman Annex community pool is approximately 100 steps from the back garden gate.
What is the minimum stay?
29 days / 28 nights. Bookings typically run Saturday to Saturday. Exceptions are made for special events such as the Key West boat races and Fantasy Fest.
Are pets allowed?
Pets are welcome by special permission from the owner. Contact directly to discuss.
Is there a smaller option available?
Yes — the owner also rents a casita (condo) six doors away in the same Truman Annex neighborhood (VRBO listing #1049465), which is a good option for smaller parties.
Amenities at A Touch of Bermuda in Key West
Non-smoking
Pets allowed
Map of Key West, FL
Ratings and reviews
10 / 10Outstanding·Oct 2025
Loved the location
10 / 10Outstanding·Aug 2025
It was great
10 / 10Outstanding·Jul 2025
Great place to stay
5 / 10·Apr 2022
Had a great stay this March in Key West. A great part of that was staying in Jack's cottage. Extremely comfortable for four people. Location was very central to everything in Old Town but far enough off Duval to cut down on the noise. Jack was a gracious host and well versed in all things Key West. Hope to get back some day.
$$$$
Top rated by guests
9.8Outstanding
(44 Ratings)
"Loved the location "
Sue J.Don't miss out! Price and availability may change
