Kaiku & Guesthouse
Cayman Kai, Cayman Islands
An eight-bedroom gated waterfront estate in Cayman Kai with a six-bedroom main house and a detached two-bedroom guest cottage.
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Cayman Islands
Vacation homes in Cayman Islands · At least 3 bedrooms
47 homes published by their hosts. Enquire or book directly with the host.
Of these 47 homes, 23 have a private pool, 33 sleep at least 8, and 22 meet both requirements. Counts reflect host-published facts; missing details are not treated as confirmed amenities. Dates and prices are confirmed on each host’s booking site.
Filter these homes47 homes · Cayman Islands
Kaiku Villa
Cayman Kai, Cayman Islands
Kaiku is a six-bedroom beachfront gated estate in Cayman Kai on the Bioluminescent Bay.
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Kailypso
Cayman Kai, Cayman Islands
A three-bedroom beachfront villa in Cayman Kai on Bio Bay, with a private pool, secluded beach, private dock and kayaks.
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Koha Kai 7BR | Luxury Platinum Villa
Cayman Kai, Cayman Islands
Koha Kai is an oceanfront villa in Cayman Kai with a heated infinity pool, white sandy beachfront, and a detached two-bedroom guest bungalow.
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Lone Palm
Gun Bay, Cayman Islands
Oceanfront villa in Gun Bay on Grand Cayman's East End with a private pool, beachfront veranda, and white-sand beach access.
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Maravilla
North Side, Cayman Islands
Maravilla is a four-bedroom, two-story oceanfront villa in North Side with direct beach access and reef-protected snorkeling from the beach.
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Moon Kai 5BR | Platinum Villa
Cayman Kai, Cayman Islands
Moon Kai is an oceanfront villa in Cayman Kai with five oceanfront suites, a private infinity pool, and direct access from the pool deck to a white sandy beach.
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Oceans 9 Villa 8
West Bay, Cayman Islands
Oceans 9 is an oceanfront villa in West Bay with four bedrooms, a courtyard pool, winding water paths, and access to an oceanfront infinity pool.
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Oceans 9 Villa 9
West Bay, Cayman Islands
Oceans 9 Villa 9 is a four-bedroom villa in West Bay with an oceanfront setting, a communal pool and water paths, and contemporary open-concept living.
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On The Rocks | 6BR
South Coast, Cayman Islands
On The Rocks is a six-bedroom gated estate in the Beach Bay community along Grand Cayman's rugged South Coast, with ocean views, a private freshwater pool and access to a shared sandy beach cove.
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Peace & Kai It
Cayman Kai, Cayman Islands
A three-bedroom beach cottage on the shores of Grand Cayman's Bioluminescent Bay in Cayman Kai, with a private dock and complimentary kayaks.
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Rip Kai Villa 7BR | Luxury Platinum Villa
Rum Point, Cayman Islands
Oceanfront villa in Rum Point with seven bedrooms, private pool and spa, beach access, extensive indoor and outdoor entertaining space, and optional guest services.
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RPR #206 | 3BR Premium
Rum Point, Cayman Islands
A three-bedroom second-floor condo at Rum Point Resort with ocean views, a private roofed balcony, and access to resort beachfront and amenities.
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RPR #403 | 3BR Premium
Rum Point, Cayman Islands
A fourth-floor, 2,250-square-foot three-bedroom condo at Rum Point Resort with ocean views, a private oceanfront balcony, resort beachfront, and a heated infinity pool.
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RPR #504 | 3BR Penthouse
Rum Point, Cayman Islands
A fifth-floor, 2,620-square-foot penthouse at Rum Point Resort in Rum Point, with ocean views, a private open-air balcony and resort beachfront amenities.
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Sea Dreams #1
West Bay, Cayman Islands
Ground-floor condo in West Bay with panoramic tropical and oceanfront views, a furnished private balcony, and walk-out access to the shared pool deck.
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Sea Dreams #4
West Bay, Cayman Islands
Second-floor corner condo in SeaDreams with elevated oceanfront views and a furnished balcony.
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Sea Dreams #5
West Bay, Cayman Islands
Sea Dreams #5 is a third-floor, three-bedroom condo in West Bay with panoramic tropical and elevated oceanfront views, a furnished private balcony, and access to shared oceanfront amenities.
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Sea Dreams #6 | New!
West Bay, Cayman Islands
A third-floor corner condo in SeaDreams with elevated oceanfront views, an oceanfront balcony, shared pool and spa access, and a walkway to the ocean over ironshore.
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Sea Dreams #8
West Bay, Cayman Islands
Sea Dreams #8 is a fourth-floor penthouse condo in West Bay with panoramic tropical and elevated oceanfront views, a furnished balcony, shared pool and spa access, and a rooftop lounge.
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SeaBreeze #3
West Bay, Cayman Islands
A second-floor, four-bedroom condo with a private ocean balcony in a residential resort on Seven Mile Beach.
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Sun Salutations | Luxury Platinum Villa
Cayman Kai, Cayman Islands
Sun Salutations is an oceanfront estate in Cayman Kai with a private infinity pool, beachfront access, ocean views, and a short barefoot stroll to the Rum Point Club.
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Villa Caymanas
North Side, Cayman Islands
Villa Caymanas is an oceanfront villa in Old Man Bay on Grand Cayman’s north coast, with four bedroom suites, a freshwater pool and nearby snorkeling reefs.
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