A Touch Of Cuba In Key West

1 / 15

2 / 15

3 / 15

4 / 15

5 / 15

6 / 15

7 / 15

8 / 15

9 / 15

10 / 15

11 / 15

12 / 15

13 / 15

14 / 15

15 / 15

2-bedroom Condo in Key West

4 guests·2 bedrooms·2 beds·1 bathroom

Hosted by Jack Agnew

Superhost·7 years hosting

Fast wifi

Reliable connection throughout the property.

Private pool

One of the few places in the area with a pool.

A Touch Of Cuba In Key West

Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two bedroom, one bathroom condominium or casita as Cubans would call it, is located on picturesque Southard Street, the main entrance to the best location on the island, the Truman Annex where you can walk to just about everything you want to see or do. I am confident you would like this vacation home away from home. It is impeccably designed, meticulously maintained and you are surrounded with restful colors on the wall and art work from my many visits to Cuba on educational and humanitarian trips. I have everything you need for a worry free island vacation. Top mattresses, high thread linens, thirsty bath towels, large deep beach towels, high speed WIFI, reserved and secure parking and cable TV. Your comfort is my first priority and between my home itself and the large back deck shaded with a large umbrella, you can "rest" assured that you will enjoy your stay. The furniture and beds are very comfortable. The kitchen fully equipped from the Bosch dishwasher to the exotic micro wave and the Keurig coffee maker. Need a hair dryer? Got it. Iron? In above the large front loading washer and dryer. Beach chairs? On the large back deck. Ask me about other amenities. And yes, there is the mandatory blender. This is my personal home so I would like to deal with you directly on email and telephone before we make a booking. Guests must come and go on a Saturday for the most part. Now on to more detail. Oh one more thing. If your party is looking for additional space, check out my cottage five doors down which is # 361238 here on VRBO. BONUS OFFER I HAVE SOME NICE OPENINGS IN SUMMER AND FALL A ALLOW ME TO OFFER A GIFT CERTIFICATE TO ONE OF KEY WEST'S BEST RESTAURANT "BLUE HEAVEN" Our prices include all fees. No hidden fees.

Where you'll sleep

What this place offers

air conditioning

balcony

bed linens provided

dishwasher

garden or backyard

hot tub

internet wifi

iron ironing board

3 nights in Key West

Add your travel dates for exact pricing

August 2026

September 2026

August 2026

Things to know

House rules

children welcome
no smoking
pets allowed

Safety & property

accessible parking
fire extinguisher available
service animal friendly

Cancellation policy

100% refund if you cancel at least 60 days before check-in.
50% refund (minus the service fee) if you cancel at least 30 days before check-in.
No refund if you cancel less than 30 days before check-in.

Damage and Incidentals
You will be responsible for any damage to the rental property caused by you or your party during your stay.

House Rules
Check in after 3:00 PM
Check out before 10:00 AM
Minimum age to rent: 25
Children
Children allowed: ages 0-17
I love families
Events
No events allowed
Pets
Pets allowed: dogs (limit 1 total)
Have an extra fee charged by to me the housekeeper
Smoking
Smoking is not permitted

$ 357night

You won't be charged yet

Final price calculated after date selection

Where you'll be

Key West, Florida, United States of America, Key West, Florida, United States

About the area Located by the sea, this condo is in Old Town Key West, a neighborhood in Key West. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching. What's nearby Duval Street - 6 min walk Ernest Hemingway Home and Museum - 7 min walk Fort Zachary Taylor Historic State Park - 8 min walk Mallory Square - 9 min walk Southernmost Point - 15 min walk Getting around Key West, FL (EYW-Key West Intl.) - 10 min drive Restaurants Santiago's Bodega - 3 min walk La Creperie - 4 min walk Margaritaville - 5 min walk Mattheessen's - 5 min walk Pinchers - 6 min walk

Meet your host

Jack Agnew

Superhost

Reviews

–

Rating

7 Years

Hosting

Response rate: 95%

Responds within a few hours

Speaks

About Jack Agnew

Hosted by Jack Agnew – Key West Cottage Rental. I’m a semi-retired guy who was in the television and marketing/public relations industry and is now a professional character actor/singer on stage, and I teach Marketing and Public Relations at a university in Boston, MA every Fall. My oldest daughter was married here in Key West, and it's a special place for me as I hope it will be for you. Why they chose this property: I always had TAE (Truman Annex envy) when my two daughters and I were visitors and renters in Key West. I vowed I'd live here one day, and when I sold my public relations firm in 1999, I bought a small two-bedroom, one-bath condo, and five years later, this much larger two-bedroom, two-bathroom cottage. I am in Key West at least six months a year and rent out my home when I am not in town. What makes this property unique: A Touch of Bermuda in Key West is my 'friend with benefits' as everything I want to see or do is within walking or biking distance. You are in walking distance to the nearby Ft. Zach beach, and the new water splash pad for children is just down at the end of the block. One couldn’t ask for more.

To help protect your payment, always use our platform to send money and communicate with hosts.

$ 357/ night