Holiday rentals in Old Man Bay

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

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.

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.

Beautiful one bedroom beach view unit with cabana

Welcome to the unique and tranquil Rea’s Vista in the Seafarers district of East End in the beautiful Cayman Islands! Enjoy the beach life, the marine life or just swimming at your own private beach where you can also see sunrise! Sunset! Moon rise! in a relaxing atmosphere enjoying the Caribbean Sea. The one bedroom unit offers WiFi, TV, washer and dryer, surveillance cameras and comes fully stocked with utensils to manage your own meals or one may choose to visit nearby local restaurants.

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.

Coral Cottage - Beach Front w/ Private Pool

Coral Cottage – Luxury Beachfront Retreat with Private Pool & Sea Views Old Man Bay, Grand Cayman | Sleeps 6 | 3 Bedrooms | 3 Bathrooms | Escape to your own slice of paradise. Nestled on the pristine beachfront of Old Man Bay, North Side. Coral Cottage is a stylish semi-detached villa offering the perfect blend of Caymanian charm and upscale comfort. With panoramic sea views, a private saltwater infinity pool, and lush gardens for al fresco dining, this is island living at its finest.

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-Bed Beachfront Condo w/ Heated Pool

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.

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.

Silver Reef #3 - 2 BR LUXE Oceanfront & Pool

The Silver Reef #3 is a new, immaculate, luxuriously furnished 2 bedroom, 2 bath oceanfront condo on the ground floor of the brand new Silver Reef Residences. Conveniently set along Grand Cayman’s scenic Northeast Coast in Old Man Bay, this modern retreat is typically about a 30–35 minute drive from Owen Roberts International Airport in George Town and sits within a thoughtfully designed, palm lined community with resort style amenities and a quiet, less traveled setting.

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!!"