Welcome to Shady Palms, a polished private retreat where historic Key West character meets relaxed island luxury. Thoughtfully restored and stylishly redesigned, this 1933 home offers a sophisticated setting for guests ready to settle into the Key West lifestyle for a month—or perhaps a little longer.

Tucked into the peaceful Meadows neighborhood, Shady Palms feels delightfully removed from the crowds while keeping the island’s restaurants, galleries, waterfront and nightlife within easy reach. Behind its white picket fence and signature red door, you’ll find a bright, beautifully curated home designed for effortless indoor-outdoor living.

The showpiece kitchen pairs soaring wood-paneled ceilings with expansive countertops, stainless-steel appliances, a gas range and seating for four around the oversized island. French doors open directly onto the pool deck, allowing morning coffee, leisurely lunches and evening cocktails to flow naturally outdoors.

The light-filled living room provides a refined but comfortable place to unwind, with plantation-style shutters, vaulted ceilings, contemporary furnishings and a large television.

The serene primary suite features a queen bed, walk-in closet and private bath with an indulgent multi-head shower. The equally inviting guest suite includes two twin beds that can be converted into a king, a walk-in closet and its own en-suite bath with a tub and shower. A separate powder room adds convenience when entertaining.

Outside, your private tropical oasis awaits. Take a dip in the heated pool, stretch out on a chaise beneath the palms or dine al fresco beside the water. A gas grill makes relaxed poolside dinners practically obligatory, while the covered front porch offers a breezy perch for morning coffee, a good book or an end-of-day cocktail.

Shady Palms also includes central air-conditioning, high-speed Wi-Fi, a washer and dryer, a fenced yard and coveted off-street parking for a medium-sized vehicle. Pets may be considered with prior approval.

For guests seeking privacy, style and an authentic residential Key West experience, Shady Palms makes an extended island stay feel wonderfully indulgent.

***Booking Information***

Important Notice: Some booking platforms may not correctly display our security deposit requirements. The rental agreement is based on a $125 non-refundable damage protection plan in lieu of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

Guests are subject to a 2% credit card processing fee. To avoid that fee, we encourage you to pay by check.