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Caroline on My Mind: Restored 1933 Home in the Heart of Old Town Key West

May 4, 2025 by Dominique Barrera Leave a Comment

Caroline on My Mind: A Restored Gem on Caroline Street 🌴

Located in the heart of Old Town Key West, “Caroline on My Mind” is a beautifully remodeled second-floor home dating back to 1933. With its storied architecture and thoughtful updates, this charming residence offers a uniquely immersive island living experience.

From the moment you ascend the wainscoted stairway to the entry, you’ll feel the historic charm mingling with tropical tranquility. Inside, the open-concept living area is bright and airy, thanks to soaring vaulted ceilings and cathedral windows that welcome in Key West’s signature sunshine.

The kitchen is both functional and inviting, featuring a flat-top electric stove, two-door refrigerator, and dishwasher—plus countertop seating for three, perfect for a casual breakfast or chatting with friends over happy hour prep.

A guest bedroom and full shower bathroom occupy the same level, along with a stacked washer and dryer for your convenience.

Step outside onto the large covered balcony overlooking lively Caroline Street. Outfitted with ceiling fans, a four-person table, and plenty of shade, it’s ideal for al fresco dining, morning coffee, or simply enjoying the island breeze while watching the world go by.

A spiral staircase leads to the upper floor, where you’ll find the serene primary bedroom nestled among the treetops. The queen-sized bed can be converted into two twins to suit your needs. A work desk with a view provides space for productivity, and a skylight above the bed invites stargazing at night—an unforgettable touch of Key West magic.

Additional features include:

  • Monthly rental only (30-day minimum)

  • Shared pool (6 units)

  • Pets are not permitted

Whether you’re staying for a month or more, “Caroline on My Mind” offers the perfect blend of historic elegance and relaxed island comfort.

Street View
Kitchen & Living Room
Living Room
Porch off living room
Pool

Filed Under: Key West Real Estate, Vacation Rentals, Vacation Rentals Tagged With: Caroline Street, Key West balcony, Key West monthly rental, Old Town Key West, restored historic home, vacation rental Key West

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