Kai Conut
Cayman Kai, Cayman Islands
A five-bedroom, single-level beachfront home in Cayman Kai with a private pool and dock.
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Cayman Islands
Vacation homes in Cayman Islands · Room for at least 4
54 homes published by their hosts. Enquire or book directly with the host.
Of these 54 homes, 25 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 homes54 homes · Cayman Islands
Kai Cove
Cayman Kai, Cayman Islands
Kai Cove is a furnished beachfront home in Cayman Kai on Grand Cayman's Bioluminescent Bay.
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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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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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Kailua
Cayman Kai, Cayman Islands
Kailua is a two-bedroom, two-bathroom waterfront condo in Cayman Kai with elevated sunset views and a screened beachfront porch.
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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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Pools of the Kai #3
Cayman Kai, Cayman Islands
A two-bedroom villa in Cayman Kai with a private pool atrium, water views, and barefoot beach access.
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Pools of the Kai #6
Cayman Kai, Cayman Islands
A two-bedroom, two-bathroom beachfront condo in Cayman Kai with water views and a private pool atrium.
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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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Rum Point Resort #105
Rum Point, Cayman Islands
Ground-floor, beach-level condo with direct beach access, ocean views, and a private ocean veranda.
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Rum Point Resort #305
Rum Point, Cayman Islands
A 2-bedroom, 2,087-square-foot condo on the third floor of Rum Point Resort in Rum Point, with ocean views, a private oceanfront balcony, resort beachfront and a heated infinity pool.
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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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