Holiday houses in Cayman Islands

Luxury Beachview Retreat, Cayman Islands

Luxurious, four bedroom, four and a half bath home with ensuite bathrooms and a half bath for guest. All bedrooms provide a private balcony with stunning oceanviews. This modern gated home in Northside is only 40mins from the airport and features a private pool, public beach access and a mini-golf course. BEDS Master on upper level has a king bed Second bedroom on upper level has a queen bed Third bedroom on upper level has 1 full bed and 3 twins Fourth bedroom on lower level has a queen bed.

North Side Grand Cayman Beachfront Villa

Spacious beachfront home on Grand Cayman’s peaceful North Side. Walk out to crystal-clear water for snorkeling and paddleboarding — we provide kayaks, paddleboards, and snorkel gear. 4 en-suite bedrooms plus two sofa beds in living room, rooftop with ocean views, fast WiFi, full kitchen, and washer/dryer. Small grocery store and Over the Edge are 1 mile away. Supermarket in Savannah (~20 min). Restaurants & bars @ Kaibo & Rum Point (~15 min). Travel crib and kids’ games available. Self check-in.

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of award winning island style cottages. This unit has a private outdoor dining and garden shower. At Botanica, our focus is on casual luxury, dreamy details and high end amenities. Property highlights includes a resort style pool with heated spa set in a tropical oasis. We also offer a complimentary shuttle in our vintage Land Rover Defender to nearby beaches. Be sure to check out our other listings under my profile. Non Smoking Complex

Adorable Boho-Style Beach Villa

This adorable studio apartment has been fully renovated & has everything you need to enjoy the perfect Caribbean getaway. Calypso Cove is directly across from the famous Seven Mile Beach, where you can swim in the crystal clear blue sea every day. The studio has a balcony so you can enjoy the sunset or a morning coffee. Walking distance to supermarket, restaurants, bank and pharmacy, this apartment is in the perfect location. Keurig coffee machine, deck chairs, fins and mask and beach umbrella.

Blissful a Luxury Ocean Front Villa, Grand Harbour

Experience Blissful, your luxurious getaway in the charming Allure community of Grand Harbour. This stylish 3-bedroom condo boasts modern comforts and features a fully-equipped kitchen, pool, and stunning ocean views. With supermarkets, a wide range of dining options and outdoor activities just minutes away, Blissful offers an unbeatable blend of convenience, relaxation and value. Whether you're here for adventure or relaxation, our condo provides the perfect unforgettable stay in Grand Cayman.

Rum Cove on the Bioluminescent Bay with Ocean View

Welcome to Rum Cove – your private escape on the bioluminescent bay, just steps from the world-famous Rum Point. This bright & breezy 1-bedroom retreat is part of a charming triplex and offers stunning 360° views. Whether you’re relaxing on the patio, kayaking under the stars, or sipping coffee at sunrise, Rum Cove surrounds you with natural beauty & peace. A perfect space for couples, solo travelers or small families looking for a quiet getaway with the best of Cayman Kai on your doorstep.

Enoe’s Escape

Welcoming 1 bedroom apartment with en-suite bathroom, sitting area, full kitchen, washer, dryer, and outdoor patio. Located in a quiet neighbourhood in close proximity to most things. 2-minute walk to the historic site Pedro St. James Castle, a stunning spot to view sunsets! 3-minute drive from the nearest supermarket and local restaurants. 5-minute drive to the picturesque Spotts Beach. 20-minute drive from other popular destinations, including shopping centres and other local attractions.

Southern Exposure, Secluded Paradise, Cayman Brac

On the Beach! Divers paradise! Beautiful slice of heaven on the exclusive south side of Cayman Brac. Stunning views from the windows - 100 ft of beachfront to call your own. The sea on one side, and the stunning and majestic bluff across the road. Pristine with luxury features to ensure you are comfortable. Local rates available! We have a 5 night minimum but please request for shorter stays. We look forward to hosting you at our island beach home! Jen & Rick IG: southernexposurecb

Whispering Kai: beach home on Bio Bay, Cayman Kai

A quiet oasis with unforgettable views. Located directly on the Bioilluminesce Bay in the wonderful residential area of Cayman Kai is our luxurious yet comfortable 2 bedroom, 2 bathroom secluded beachfront home complete with a spacious screened-in back patio overlooking the water on a white sandy beach with a private boat dock. Check us out on Insta: @whisperingkai Master Bedroom: King Bed Guest Bedroom: King Bed plus two pull-out sofas (twins) Living Room: One pull-out sofa (double)

Modern Island Studio | Peaceful Garden Hideaway

Quiet private cottage in a safe residential neighborhood, just minutes from beaches, restaurants, and grocery stores. Slip away to this cozy studio tucked in peaceful Red Bay—an ideal retreat for couples or solo travelers. Unwind in a plush queen bed, stream on smart TV, and enjoy the ease of a private entrance and free parking. Just minutes from the airport, grocery stores, George Town, and top dining spots, you’re perfectly placed for both relaxation and adventure.

Luxury 3 Bedroom Waterfront Condo in Paradise

Modern 3BR/3BA waterfront home offering luxury, comfort, and uninterrupted ocean views. Enjoy morning coffee as waves roll in and end your day sipping wine with breathtaking Caribbean sunsets off your private patio area. The complex features a pool, hot tub, gym and lounge areas, all set in a welcoming neighbourhood just a 2-minute walk to Cayman’s favourite tiki bar. A stylish retreat perfect for families, couples, or friends seeking a refined island stay.

Paradise Beach House in South Sound, George Town

Paradise Beach House in South Sound, George Town Paradise Beach House is a beautiful vacation rental property located in South Sound, George Town, Grand Cayman. The house offers a spacious and luxurious living experience with its very own paradise beach and a view of the reef and famous wreck of South Sound! Please note the "Resort Fee" is the Government Tourist Tax that is charged to all international guests staying in the Cayman Islands.