Holiday houses in Old Man Bay

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Top-rated holiday rentals in Old Man Bay

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Top Guest favourite
The exterior of the cottage is framed by vibrant tropical plants and flowering shrubs, showcasing a blend of lush greenery and colorful blooms. The white structure features a sloping roof, supported by two elegant columns at the entrance.
Cottage in West Bay
4.99 out of 5 average rating, 371 reviews

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

Guest favourite
A screened-in patio features a colorful area rug and seating arrangement with patterned cushions. A ceiling fan is visible above, while views of the lush garden and cove are framed by large glass panels. Kayaks and lounge chairs are positioned outside, enhancing the outdoor atmosphere.
Apartment in Cayman Kai
4.93 out of 5 average rating, 228 reviews

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.

Top Guest favourite
Cottage in East End
4.98 out of 5 average rating, 121 reviews

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.

Top Guest favourite
The entrance features a dark front door framed by two windows with black shutters. Potted plants are positioned on either side of the door, adding greenery to the wooden facade. The porch is supported by two white columns, creating a welcoming appearance.
Apartment in Savannah
4.99 out of 5 average rating, 127 reviews

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.

Top Guest favourite
A vibrant turquoise fence leads to a sandy beach, with gentle waves lapping at the shore. The sky is filled with soft, white clouds, creating a serene coastal scene. The beach is just beyond the fence, inviting relaxation and enjoyment of the ocean views.
Apartment in West Bay
4.93 out of 5 average rating, 107 reviews

1 Bed Beach Rental 20 steps to the Beach!

Newly renovated 1 bedroom apartment just 50 feet to Seven Mile Beach in West Bay. From the balcony you have a partial beach view. This apartment has everything you will need for a comfortable stay and the memory foam mattress will ensure a great nights sleep. Alfresco Restaurant is across the street and Camana Bay is an 8 minute drive away. There is also a comfortable sofa bed in the living room with a queen memory foam mattress for extra guests. There is also a Shared Laundry Room on site.

Top Guest favourite
An infinity pool reflects the vibrant colors of the sunset over the sea, surrounded by palm trees. Three transparent float loungers gently rest on the water's surface, creating a serene atmosphere. The calm ocean horizon is visible in the background, complementing the tranquil setting.
Home in Old Man Bay
5 out of 5 average rating, 20 reviews

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.

Top Guest favourite
A serene view of the turquoise ocean stretches beyond a well-maintained pool area. Lush palm trees and vibrant greenery frame the space, with a sandy beach visible nearby. The outdoor seating area is partially shaded, creating a relaxing atmosphere for guests.
Holiday home in Bodden Town
5 out of 5 average rating, 109 reviews

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,

Top Guest favourite
An oceanfront view showcases a sandy beach lined with lounge chairs, framed by palm trees. A light green three-story building stands in the background, overlooking the sea. The sky is bright with scattered clouds, enhancing the tranquil coastal atmosphere.
Condo in KY
4.89 out of 5 average rating, 27 reviews

On the Bay #103 Ocean Front Condo on Northside

On the Bay #103 is a bright and spacious 3-bedroom, 3-bath ground-floor condo nestled in a lush, tropical beachfront resort in Old Man Bay. With views of the gardens and ocean, a private patio, direct access to the resort’s pool, and just steps from a protected swimming cove, this property offers the perfect blend of island tranquility and comfort. Ideal for families or groups seeking an alternative to Seven Mile Beach, while remaining within 10 minutes of Rum Point and nearby dining.

Guest favourite
Three white lounge chairs are positioned on a sandy beach, facing the calm turquoise waters of the Caribbean Sea. Lush palm trees surround the area, under a bright blue sky dotted with fluffy white clouds, enhancing the serene coastal atmosphere.
Condo in North Side
4.9 out of 5 average rating, 52 reviews

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.

Guest favourite
Home in Old Man Bay
5 out of 5 average rating, 8 reviews

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.

Top Guest favourite
An outdoor dining area is presented under a vibrant teal umbrella, featuring a glass-top table surrounded by several green chairs. The view beyond includes sandy beach and the Caribbean Sea, framed by palm trees and coastal vegetation.
Condo in Rum Point
4.94 out of 5 average rating, 162 reviews

Nature's View: Pools of the Kai #2

Discover the peaceful Caribbean paradise of Cayman Kai. This secluded oasis will put you at ease as soon as you walk through the door. Our beach front property features stunning views across the Caribbean Sea to an unspoiled nature reserve. The double story screened in private pool deck can't be beat. Perfect for family holidays or a romantic getaway. Savor heavenly mornings and sundowners on your master bedroom balcony. Stroll down the beach to Kaibo, true barefoot living!

Guest favourite
A serene beachfront scene features clean white sand gently sloping to a clear turquoise sea. Lush palm trees provide shade along the shore, while a rocky outcrop is visible in the water. Beach chairs are arranged invitingly, offering views of the tranquil coastline.
Apartment in North Side
5 out of 5 average rating, 23 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.

Popular amenities for Old Man Bay holiday rentals