Holiday houses in Old Man Bay

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Old Man Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Townhouse in Old Man Bay

4.91 out of 5 average rating, 55 reviews

Your Oceanside Retreat Awaits!

Welcome to On The Bay Condo, located on the ocean’s edge in Old Man Bay, Grand Cayman Island. This is a truly private and tranquil resort, with a lovely white sandy beach, private swimming cove, pool and, of course, the magnificent aqua-blue water of the Caribbean all at your convenience. As pristine as the location is, this condo is only 30 minutes from the International Airport in George Town, and just minutes from various restaurants, water sports, snorkeling, scuba diving and sailing trips.

Guest favourite

Guest suite in Grand Cayman

4.96 out of 5 average rating, 51 reviews

Studio 1 @ Fort Rocks, Forest King near beach!

STUDIO 1 has amazing natural rock & forest views, WiFi, electricity, water, AC, King bed, seating area, dining area, SMART flat screen TV, portable induction hot plate, coffee maker, toaster oven w/air fryer, microwave, bread toaster, dishwasher, fridge/freezer, compact washer/dryer, private back patio & large two level deck (with deck net) perfect for yoga, morning coffee or just relaxing. Fire pit & BBQ grill. 1 parking space. Close to beaches, restaurants, local attractions, shops & schools.

Guest favourite

Rental unit in East End

4.98 out of 5 average rating, 43 reviews

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

4.98 out of 5 average rating, 211 reviews

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.

Superhost

Condo in North Side

4.9 out of 5 average rating, 39 reviews

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

Rental unit in North Side

5 out of 5 average rating, 5 reviews

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

Guesthouse in Grand Harbour

4.99 out of 5 average rating, 138 reviews

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

Home in North Side

5 out of 5 average rating, 35 reviews

Private oceanfront home wraparound screened porch

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 air concept. Relax on the 360 degree wraparound screened porch which has two seating areas both boasting oceanfront views of the Caribbean Sea. Direct water access into the sea. Separate primary suite for ultimate privacy. Located on 1+ acres. Free kayaks.

Guest favourite

Rental unit in East End

4.93 out of 5 average rating, 14 reviews

Spacious Oceanfront Studio

Take a break and unwind at this peaceful studio overlooking the sea from your 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 George Town

4.88 out of 5 average rating, 77 reviews

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

Rental unit in GRAND CAYMAN

4.93 out of 5 average rating, 200 reviews

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

4.96 out of 5 average rating, 146 reviews

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.