Cayman Islands Holiday Homes

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Featured Holiday Homes in Cayman Islands

Azure Breeze #4, Beachfront, White Sand, Bikes, Kayak, Snorkel Gear, Rum Point!!

North Side Cayman Islands

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During your stay at this holiday home, you're just a quick walk from Grand Cayman Beaches. Laundry facilities are available. Enjoy your stay with amenities like a kitchen and 2 bathrooms in the holiday home.

Küche

Waschmaschine

So Serene Oceanfront Villa, Rum Point, Private Beach, Hot Tub, Kayak, Snorkeling

Grand Cayman North Side

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During your stay at this holiday home, you're just a quick walk from Cayman Kai Public Beach. Enjoy features like 1 hot tub, concierge services and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Whirlpool

Küche

Escape,Enjoy,Unwind to Kailegría, 2BR,2BA condo in Cayman Kai’s Kaibo Yacht Club

Rum Point Grand Cayman

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During your stay at this holiday home, you're just a quick walk from North Sound. You'll find features such as 1 hot tub and laundry facilities. The holiday home offers a kitchen and 2 bathrooms.

Pool

Whirlpool

Ocean Paradise

1234 Rum Point Road North Side Grand Cayman

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During your stay at Ocean Paradise, you're just a quick walk from North Sound. Free WiFi in public areas, free self-parking and an outdoor pool are available. This upmarket holiday home has 3 homes. Enjoy your stay with amenities like free WiFi and a kitchen in each holiday home.

Pool

Küche

CORAL VISTA - Infinity Pool, Arcade, Theater, Private Cabana

North Side

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During your stay at this holiday home, you're just a quick walk from Grand Cayman Beaches. Features include an indoor pool, a swim-up bar and breakfast (surcharge). The holiday home offers a private pool and a kitchen.

Pool

Küche

BEACHFRONT w/ Private Dock-50 ft Pool-Theatre

Northside

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During your stay at this holiday home, you're just a quick walk from Grand Cayman Beaches. Features include an outdoor pool and laundry facilities. Enjoy your stay with amenities like a private pool and a kitchen in the holiday home.

Pool

Küche

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

Rum Point Grand Cayman

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During your stay at this holiday home, you're just a quick walk from Grand Cayman Beaches. Enjoy features like an outdoor pool and laundry facilities. The holiday home includes amenities such as a private pool and a kitchen.

Pool

Küche

50% off 4th night! Private, quiet oceanfront home, wrap-around screened porch.

North Side Grand Cayman

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During your stay at this holiday home, you're just a quick walk from Babylon (Dive Site). Laundry facilities are available. The holiday home offers free WiFi and a kitchen.

Küche

Waschmaschine

Slice of Paradise- 2 mins from Spotts Beach!

Patricks Island George Town

CHF 137

10 Jan - 11 Jan 2026

includes taxes & fees

During your stay at this holiday home, you'll be within walking distance of Grand Cayman Beaches. Enjoy your stay with amenities like free WiFi and a kitchenette in the holiday home.

Küche

Waschmaschine

Island House #16 Waterfront Condo at Rum Point

Rum Point EA

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During your stay at this holiday home, you're just a quick walk from Rum Point Beach. You'll find features such as laundry facilities. Enjoy your stay with amenities like a kitchen and a washer/dryer in the holiday home.

Pool

Küche

Country Road, Take me Home- your own Island Cottage!

Savannah

CHF 146

18 Dec - 19 Dec

includes taxes & fees

During your stay at this holiday home, you'll be within walking distance of Pedro St. James National Historic Site. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Küche

Haustierfreundlich

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!

Cayman Islands

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During your stay at this holiday home, you're just a quick walk from North Sound. An outdoor pool and laundry facilities are available. The holiday home includes amenities such as free WiFi and a private pool.

Pool

Küche

Caymanian Style Home w/ Pool, Pickle Ball Court, Optional Private Bar

Rumpoint Grand Cayman

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Our customers tell us that they can't get enough of the helpful staff at this holiday home. During your stay, you're just a quick walk from North Sound. Features include an outdoor pool, laundry facilities and an arcade/games room. The holiday home includes amenities such as free WiFi and a private pool.

Pool

Küche

Caribbean Vacation Family Private Beach House /Sunset/ RumPoint/StarFish Point

Grand Cayman Grand Cayman

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During your stay at this holiday home, you're just a quick walk from North Sound. Features include 1 hot tub and laundry facilities. The holiday home includes amenities such as free WiFi and a kitchen.

Pool

Whirlpool

You'So Breezy: New Beach House w/ Pool, & Backyard Snorkeling! Next to Ocean Fro

Gun Bay East End

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During your stay at this holiday home, you're just a quick walk from Grand Cayman Beaches. You'll find features such as a gym and laundry facilities. The holiday home includes amenities such as free WiFi and a private pool.

Pool

Küche

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.