Stay together — and still have space to breathe: Four Key West homes perfect for group travel

Casablanca Grande — a double dose of island comfort

Tucked on the edge of Old Town in a quiet residential neighborhood, Casablanca Grande combines the best of both worlds: two adjoining sides of a classic Key West duplex, joined by a large pool and private hot tub. Each side offers its own kitchen, living room and king bedroom with ensuite bath — so you can vacation together without tripping over each other’s beach bags. Enjoy coffee on the porch, cook out on the grill, or lounge by the pool before a 15-minute stroll to Duval Street. Because sometimes the secret to harmony is two kitchens and two front doors! Pet friendly: one dog welcome (up to 25 lbs).

Poinciana Paradise — just steps from the action

Just two blocks from Duval Street, Poinciana Paradise is a Key West dream for friends or families who love being near the action but crave a quiet retreat at day’s end. This colorful, 2BR, 2BA duplex offers two independent spaces — each with a full kitchen, private porch, and charming French doors that open to the lush garden below. Whether you rent one level or both, you’ll have room to spread out, recharge, and reconnect at your own pace. Perfect for couples traveling together or extended families who want to balance together time with downtime. Pet friendly: one dog welcome (up to 25 lbs).

Queen Conch — three units, one royal stay

If your group loves the idea of staying together in a historic home that feels like pure Key West magic, Queen Conch is the crown jewel. This beautiful two-story “eyebrow” house features three separate units — Horse Conch, Rooster Conch and Sea Conch — centered around a lush pool and tropical courtyard. Rent all three for exclusive use and enjoy four bedrooms, four baths, three kitchens, and room for up to 14 guests. Spend the day exploring nearby shops and cafes, then gather for dinner by the pool or sunset cocktails on the shared balcony. You’ll have privacy when you want it — and paradise just outside your door.

Solaris Pair-A-Dise — Bohemian bliss for friends and family

Tucked along a quiet Old Town lane, Solaris Pair-A-Dise is full of local color and artistic flair. This laid-back duplex features two self-contained 1BR spaces — Solaris Cottage and Solaris Garden — each with its own entrance, kitchen, and sunny island vibe. Spend mornings under the banyan tree with coffee in hand, and evenings grilling out in the shared garden. The location puts you just a short walk from Duval Street, Mallory Square, and all the island’s top attractions — but it feels like your own secret hideaway. Perfect for two couples, small families, or friends who love to share the adventure while keeping their own cozy corner of paradise. Pet friendly: one dog welcome (up to 25 lbs).

The Key West way to vacation together

When it comes to traveling with your favorite people, sometimes a little personal space makes the best memories. These four properties let you stay connected, comfortable, and completely at ease — whether that means poolside cocktails, solo naps, or late-night stories under the stars. Bring your family, your best friends, even your pup — and experience the joy of vacationing together … separately. Start planning your group getaway today at HistoricKeyWestVacationRentals.com.

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Stay together — and still have space to breathe: Four Key West homes perfect for group travel

Casablanca Grande — a double dose of island comfort

Poinciana Paradise — just steps from the action

Queen Conch — three units, one royal stay

Solaris Pair-A-Dise — Bohemian bliss for friends and family

The Key West way to vacation together

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