Smiling House brings together 4 hand-selected luxury apartments in Cayman — each one chosen for its setting, its design and the service around it. Cayman is a polished Caribbean haven of powder-soft beaches, calm turquoise water and world-class diving. From intimate hideaways for two to expansive homes for family and friends, every apartment is booked directly with our team — no middle-man, no surprises. Browse the homes below, then speak to a concierge who knows Cayman first-hand about dates, rates and the details that make a stay effortless.
There is temporarily no availability for luxury apartments in cayman. New homes join the collection regularly — explore the full search or a nearby selection below.
More to rent in Cayman
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Frequently asked
- How do I book a apartment in Cayman?
- Choose a home below and send an enquiry, or ask to book directly. A Smiling House concierge confirms availability and rates with the owner and handles the booking end to end — you deal with our team, not a faceless platform.
- What's included when I rent a apartment in Cayman?
- Every home is fully furnished and privately yours for the stay. Concierge support, and often housekeeping and local recommendations, come as standard; specific services vary by property and are listed on each home's page.
- Is it cheaper to book direct with Smiling House?
- Booking direct removes the platform mark-ups that sit on OTA listings, and puts you in touch with a team that knows Cayman personally. You get the real home, the real price and a human who answers.
- How many apartments are available in Cayman?
- 4 apartments are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.