A holiday that feels like yours
The biggest shift with an extended stay isn’t what you do, it’s how it feels.
There’s no urgency to “fit everything in” and no pressure to make every moment count, and no sense that time is slipping away. Instead, you’ll find space to reconnect with family, to enjoy quiet mornings and lively evenings, and to create traditions that are entirely your own.
By the time the holidays arrive, you’re not arriving, you’re already there. You’ll feel at home and part of a unique community for an entire month. It’s an experience you and your family will always remember.
This December, let us help you select the ideal accommodation from our collection of fine homes in Old Town Key West. Here’s a small sampling of what’s available now:
● California Dreaming: This luxurious 4BR, 3BA designer home combines sophisticated California-inspired style with classic Key West architecture. It features a private heated saline pool, stunning chef’s kitchen with a 6-burner Bertazzoni range, multiple porches and balconies, and a dedicated office with dual workstations for remote work or studying. With elegant interiors, lush landscaping, and easy access to the White Street Pier and southern Duval Street, this home offers an elevated island experience perfect for extended family stays.
● Blue Haven: Guests who crave privacy will love this spacious 4BR, 3BA monthly rental designed for comfort and upscale outdoor living. This beautifully updated home features an open-concept layout, a gourmet kitchen, Italian leather furnishings, and a separate guest cottage complete with its own kitchenette and ensuite bath. Outside, guests can unwind around the private pool, lush tropical landscaping, outdoor dining area, and fire pit, creating the perfect setting for extended stays with family or friends.
● Sunset Cove: A stunning waterfront 2BR, 3BA townhome is designed for relaxed indoor-outdoor island living. This monthly rental features a private seasonally heated pool, oversized lanai, balconies off both ensuite bedrooms, and direct water access with a private dock for a 25-foot boat or kayak launching. Inside, the bright, open design includes stainless steel appliances, comfortable gathering spaces, and a bonus office ideal for remote work. Guests love the peaceful waterfront setting and the ability to enjoy spectacular sunsets just steps from their back door.
● La Casita en Cima: This beautifully restored 2BR, 2BA historic cottage is just two blocks from Duval Street in Old Town. Recipient of the Historic Florida Keys Foundation Preservation Award, this charming monthly rental combines classic Conch architecture with modern luxury amenities, including a private heated pool with waterfall feature, covered lanai and lush tropical gardens. Inside, guests will find bright interiors, hardwood floors, a farmhouse-style kitchen, vaulted ceilings, and comfortable spaces designed for both relaxation and remote work.