Vacation
Mode On
Discover thoughtfully curated homes that capture charm, character and the laid-back luxury of Key West. From historic conch houses to tropical island retreats, each stay is locally managed with personalized hospitality and insider recommendations to help you experience the island like a local.
Casa Key West Collection
Lovely Day Chalet - 908 Catherine St
Escape to The Lovely Day Chalet, a renovated 3BR/3.5BA retreat in Old Town Key West. Enjoy cathedral ceilings, open living, and a chef’s kitchen. Relax in your private oasis with a heated/chilled saltwater pool, waterfall, lush landscaping, and mango tree. Each bedroom has an en suite. Walk to Duval, beaches, and dining—then unwind in island luxury.
8 guests, 3 bedrooms, 3.5 bathrooms.
*minimum 28 day rental required
1708 Laird Street
Experience modern island living in this secluded four-bedroom Midtown gem, featuring sleek contemporary interiors and a private saltwater pool. Large glass doors create a seamless flow between the chic designer kitchen and lush outdoor terrace, offering a peaceful sanctuary for your extended stay. It is the perfect blend of sophisticated style and creative energy for a month of pure relaxation.
Your Island Escape Elevated
Private Boat Charters
Set sail for secluded sandbars, golden sunset cruises, and fishing charters designed to create forever memories on the water.
Bike, Scooter & Golf Cart Rentals
Navigate Key West with ease and joy. Access premier rentals for effortless, car-free exploring and fun island-wide adventures.
Dinner Reservations
Enjoy effortless dining with the many options for a true Key West culinary experience. Ask about our favorite local spots.
Spa Appointments
Unwind with bespoke massages and luxury beauty rituals delivered to your door for the ultimate pampered island experience. Or visit one of the many top tier spas in Key West.
Grocery Stock
Step into a kitchen filled with your favorite essentials and local island delicacies for a seamless, stress-free arrival.
Airport Transfer
Begin your stay with ease via private, pre-arranged transport, ensuring a seamless journey from the runway to our coastal door.
