Fresh Homemade Complimentary Cinnamon Rolls

About Us

Experience a beautifully restored Old Key West guesthouse rich with history...

Resident Guesthouse kitty resting peacefully

Immerse a way of life!!


The Angelina is friendly and clean, no phones or television, two blocks from Duval, within walking distance of the significant sights of old Key West.

The heated lagoon style pool, surrounded by lush tropical plants is a great place to relax and get away from it all.  Lay in our poolside hammock while the trickling waterfall lulls you to sleep. Enjoy a good book while sitting by the pool or just sip a drink while relaxing in the pool and watching the palms sway in a gentle breeze.

Your hosts will greet you with warm southern hospitality that makes you feel like you are visiting long lost family members.  Start your morning with bagels, fruit, coffee, tea, juice and of course, our famous homemade cinnamon rolls.  Then we can help you plan your stay by discussing the many things Key West has to offer from fishing, diving and snorkeling to touring historic sites to enjoying the Key West nightlife.  We can help you arrange any activity while you relax by the pool.

Adults Only...The Angelina is an adults only guesthouse. We respectfully welcome young adults starting at 18 years of age. 

Please Note... that whether intended or not, large groups are disruptive to other guests that are here to enjoy a quiet and relaxing time. We ask that all partying be done on Duval Street and not at the Angelina.


" Welcome to, Welcome back, Welcome home."

Angelina Guesthouse owners Kevin and Janet Life

Kevin and Janet Life

Hello, we are Kevin and Janet Life and we have owned the Angelina Guesthouse since October 2001.
We are from Kentucky where Kevin was an accountant and Janet was an RN. Our first visit to Key West was in 1992 while on a cruise and we loved it. We returned many times and our vacations here became longer with each visit. Due to allergies, stressful jobs and dislike for cold weather, we decided to move to Key West.
We loaded up a U-Haul truck and 4 cats and the rest is history!

We have no regrets. We truly love Key West. It is always a joy to greet new guests and welcome back guests that have become friends. We look forward to welcoming you to the Angelina Guesthouse.