Diver's Dream - Grand CaymanN°001
Cayman, Cayman Islands
Grand Cayman
Sea viewAir conditioning
From $459 per night
Smiling House brings together 4 hand-selected luxury condos 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 condo 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
1 Bdr Penthouse Oceanfront Condo w/ Infinity PoolN°002
Cayman, Cayman Islands
West Bay
Sea viewAir conditioning
From $459 per night
Modern Penthouse Oceanfront 1 Bdr Condo /w PoolN°003
Cayman, Cayman Islands
West Bay
Sea viewAir conditioning
From $459 per night
Modern Oceanfront 1 Bdr Condo /w Pool + DivingN°004
Cayman, Cayman Islands
West Bay
Sea viewAir conditioning
From $459 per night
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.
More to rent in Cayman
Condos in other destinations
Frequently asked
How do I book a condo 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 condo 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 condos are available in Cayman?
4 condos are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.