Water View 2 Bed Apt Near Beach w/ PoolN°001
Cayman, Cayman Islands
West Bay
Sea viewAir conditioning
From $459 per night
Smiling House brings together 1 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.
Updated September 2026
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.
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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?
1 apartments are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.