Holiday houses in Old Man Bay

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Top-rated holiday rentals in Old Man Bay

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Guest favourite

Villa in Old Man Bay

Old Man Bay Villa #2

Tucked away in a corner of Northside, Grand Cayman, is the quaint little community of Old Man Bay, where time has stood still. This is the authentic Cayman, no crowds and the only thing you'll hear are the ocean waves. The 2 side-by-side 1 bedroom villas are identical in layout. The main floor has a living room with queen size sofa bed, flat screen TV, fully equipped kitchen with Dishwasher & powder room. The spacious bedroom is on the 2nd floor and has a full ensuite with a large shower.

Guest favourite

Rental unit in East End

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.

Guest favourite

Guest suite in Savannah

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing.

Guest favourite

Condo in North Side

Spacious 2-Bedroom 2-Bathroom Beachfront Condo wit

The 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.

Guest favourite

Home in North Side

FREE Night! Private oceanfront home screened porch

FREE NIGHT. Book at least 3 nights and get a 4th night free (stays June - October 2024). Breezy Bay is an oceanfront, private, single-level 3 bedroom home in North Side (Old Man Bay) perfect for your relaxing Grand Cayman vacation. Enjoy panoramic oceanfront views from this beach house with a bright, open concept. Relax on the 360 degree wraparound screened porch which has two seating areas both boasting oceanfront views of the Caribbean Sea. Over 175 ft of private oceanfront living.

Guest favourite

Rental unit in North Side

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.

Guest favourite

Rental unit in East End

Spacious Oceanfront Studio

Take a break and unwind at this peaceful studio overlooking the sea from your private patio. The studio boasts unparalleled views with a bathroom, king size bed and a kitchenette. Set within the Reef Resort, enjoy lazing the day on the beach, snorkelling or diving. The property boasts a lively bar, restaurant with daily menus, coffee shop, spa, and fitness centre. You also have a small market and adult beverage store just across the street! Come join us in Cayman!!!

Guest favourite

Guesthouse in Grand Harbour

Heavenly Suite 2 - The M @ The Edge

Heavenly Suíte #2 at The M @ The Edge is a studio apartment with sleek & modern furnishings, smart HD TV, sound bar, chandeliers, state of the art kitchenette with quartz counter-tops, Delta faucet, and under counter lights. The chic bedroom fashioned in white crisp tiles, scones and recessed lighting mimics the luxurious bath styled in porcelain & Carrera tiles, Delta faucets, mirrors. . The patio enlivened by red/white accents, greenery, bar, pergolas, and Jacuzzi.

Guest favourite

Guesthouse in George Town

Zen Den 3, cozy private studio in George Town

Welcome to this private cozy studio in the vibrant heart of George Town! Lokated 10-15 minute walking distance to Smiths Cove Beach, this is separate unit with an independent entry. Has a bedroom, kitchenette, washer dryer, bathroom and designated parking spot. Located in George Town near hospitals, pharmacy, gas station and restaurants. Bedroom has queen bed, split A/C, smart TV and Internet. Private outside patio with seating and a hammock.

Guest favourite

Cottage in East End

Piece of Mine, Beachfront Villa #3

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 throughout the property. Modern walk-in Shower, Towels, and bathrobe. Full Kitchen, Keurig & regular coffee maker & Blender, Extra-large bedroom, Antique four post bed, Desk + smart TV. Enjoy paradise & experience "True Caymanian Hospitality!!"

Guest favourite

Rental unit in GRAND CAYMAN

Rum Cove on the Bioluminescent Bay with Ocean View

Beautiful Rum Cove is located next to two one bedroom Villas and it's nicely decorated to suit our Island living, which is quiet and friendly to all who come to live amounts us. Rum Cove sit's in the beautiful Cove where the famous Bioluminescent Bay sits in your backyard. We welcome you to Rum Cove and want to offer you our Cayman Kind. Rum Point Beach Bar and Fine Dining Restaurant is located across the street from Rum Cove.

Guest favourite

Cottage in Savannah

John John's Hideaway

Cozy 1 bedroom cottage with en-suite bathroom, sitting area, full kitchen, washer and dryer. Located in a quiet neighbourhood, a 2 minute walk away from Pedro St. James Castle. 3 minute drive from a supermarket and local restaurants. 5 minute drive to snorkel at the picturesque Spotts Beach. 20 minute drive from other popular destinations, including shopping centres and other local attractions.