
Holiday houses in Old Man Bay
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Top-rated holiday rentals in Old Man Bay
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Luxury Cottage, 1bd/1ba, desk | Pool+7 Mile Beach
Our King 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.

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.

Waterfront Sanctuary Serene | 2BR | Pool & Porch
Cool clean contemporary Sanctuary with water views; a two bedroom/two bathroom condo with a full kitchen and living room packed with all popular amenities (wifi, cable television, Apple TV, Netflix, Playstation game console, central A/C, iron and ironing board, washer and dryer, outdoor patio, pool and free parking) - conveniently located in Grand Harbour. The Shoppes at Grand Harbour, & Harbour Walk are next door. Perfect for exploring and enjoying all that the Cayman Islands has to offer.

Hidden Gem Cottage on the Beach
Hidden Gem is a Traditional Cayman Style cottage located at Grapetree Cove on a beautiful beach area in sleepy fishing village of East End. The property is filled with trees that gives it a dreamy Island ambiance. The Cottage has been fully renovated with modern amenities that makes is very comfortable and homey. Hidden Gem offers a unique CaymanKind experience from a Caymanian host that knows the area well. Located minutes away from local dinning places and many key attractions in the area.

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.

Art Beach House, boutique style luxury.
Private getaway for couples or singles perfect for honeymooners situated at beautiful frank sound. 25 mins from George town so car essential, many attractions nearby include the crystal caves 5 mins botanical gardens and rum point, and the beautiful east end. we also boast some of the the best dining on island. So lots to do or just chill on your private beach away from the crowds. the apartment is situated on ground floor level with art studio/Gallery above. with exclusive use of pool,

Spacious 2-Bedroom 2-Bathroom Beachfront Condo wit
This two 2-bedroom condominium located in Old Man Bay on the North Side of Grand Cayman is nestled in a prime oceanfront location. Step into this expansive unit boasting over 1,685 sq ft of living space, including a generously sized balcony that offers panoramic and uninterrupted vistas of the magnificent Caribbean Sea. Immerse yourself in the breathtaking views not only from the balcony, but also from the comfort of the living room and kitchen, creating a truly mesmerizing experience.

Beach House & Cottage - The Bay
The Bay is a private home with 500 Feet of beach front over 5 acres in the laid-back Old Man Bay community on the North Side. 3 Acre protected beach next door. Beach Access: Nearby sandy shallow water cove at On the Bay condos and excellent sandy coral reefs 100 yards down the beach. Large screened-in patio, private oceanfront saltwater pool, gazebo with twin hammocks and lounge chairs. White sand beach adjoining an extended beach along the North Side. Countless activities.

On The Bay 310 - Enjoy the View
Pristine beachfront condo with large bedrooms and master bath. On the Bay is one of the nicest condo complexes on the Northern Coastline of Grand Cayman. It has beautiful and lush tropical landscaping, which is maintained daily, and a beautiful beach located in a cove directly in front of the apartment complex with clean white sand. Enjoy the large pool and cabana with BBQ area for your convenience. Restaurants, diving, water sports and grocery stores are a 10 min drive away.

Piece of Mine, Beachfront Villa #3
Private & Tranquil BEACHFRONT Cottage offers all the conveniences of a luxury home. KAYAKS and SNORKELING GEAR, daybed & smart TV on the SCREENED PORCH, beach chairs, beach swing, and beautiful SUNSETS. Hammocks are throughout the property. Modern walk-in Shower, Towels, and bathrobe. Full Kitchen, Keurig & regular coffee maker & Blender, Extra-large bedroom, Caribbean Antique four-post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"

North Side Studio Apartment
This charming studio apartment offers everything you need for a comfortable stay in the tranquil North Side. Just minutes from the world-famous Crystal Caves, this retreat is ideal for couples or solo travelers looking for peace, relaxation, and easy access to adventure. Guests will also enjoy the convenience of a private entrance, a comfortable seating area, and thoughtful amenities for a home-away-from-home feel.

The Mastic Chapel LUXE Cottage & Pool on North Sid
The Mastic Chapel Cottage is a Ground-Floor, 2-Bedroom 2-bathroom Chapel Cottage on North Side on 11 Acres at the Cayman Mastic Trail. The cottage boasts a serene setting and is surrounded by lush vegetation, offering guests a tranquil and immersive experience.
Popular amenities for Old Man Bay holiday rentals
Other great holiday rentals in Old Man Bay

Gorgeous Sandy Beachfront at Azure Breeze Villas

Luxury + Comfort + Water View + Pool + BBQ + Patio

Beautiful beachfront, romantic get away!

*Beachfront* Coco Sands - 2 bed condo at Rum Point

Sail Away- bright modern cozy apt in North Side

4 Bedroom home on private nature reserve

Oceanfront Dreamsicle Villa w/Outdoor Living Area

Beach front condo, steps away from the sand!
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