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Search Holiday Rentals in Old Man Bay

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Old Man Bay holiday rentals

Beachfront Condo | Terrace/patio
On The Bay

Condo in North Side

On The Bay
4.0 star property
10.0 out of 10, Exceptional, (6)
"We love how secluded the condo was and it was even better that there were only one other unit rented at the same time. It was like our own private resort. The condo was huge and spotless and the view was amazing. This was exactly the trip we wanted to have!"
United States
Nick
The price is ฿17,990
฿28,352 total
includes taxes & fees
18 Jan - 19 Jan 2026
On The Bay
2 outdoor pools
Cayman Luxury Rentals at One Canal Point

Villa in Seven Mile Beach

Cayman Luxury Rentals at One Canal Point
4.0 star property
10.0 out of 10, Exceptional, (6)
"The property is pristine! We had a great stay! "
United States
Kathleen
The price is ฿35,917
฿49,625 total
includes taxes & fees
28 Dec - 29 Dec
Cayman Luxury Rentals at One Canal Point
Exterior
Cayman Luxury Rentals at Sunset Cove

Condo resort in Seven Mile Beach

Cayman Luxury Rentals at Sunset Cove
3.5 star property
The price is ฿60,663
฿83,175 total
includes taxes & fees
16 Jan - 17 Jan 2026
Cayman Luxury Rentals at Sunset Cove
Outdoor pool, pool loungers
Ocean Paradise

Holiday Home in North Side

Ocean Paradise
4.0 star property
9.6 out of 10, Exceptional, (38)
"Wonderful property! We enjoyed our stay very much! "
United States
Ashley
Ocean Paradise
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Old Man Bay Hotel Reviews

The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

10/10 Excellent
"The best ever place I have ever stayed. Staff are behind the best. Food only Italy beats them. Facility is amazing."
alessandro 6-night trip
Posted 1 day ago
The Ritz-Carlton, Grand Cayman

Find out more about Old Man Bay

Search for holiday rentals in Old Man Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Man Bay using one of the methods below:

  • View our selection of featured holiday rentals in Old Man Bay
  • Use the map to find apartments and other holiday homes in the Old Man Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Old Man Bay while they last

Look no further and take a look at our great range of rental properties in Old Man Bay!

Frequently asked questions

Are there holiday rentals in Old Man Bay?

Yes, there are holiday rentals close to the most popular sights in Old Man Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Old Man Bay has to offer?

Ocean Paradise: This holiday home rental outside of Old Man Bay is located by the ocean, and has an outdoor pool, a private balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family. It offers a terrace, a private garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Old Man Bay?

Choose from 9 Expedia holiday rentals in Old Man Bay for a memorable holiday.

What’s there to see and do in Old Man Bay?

Grand Cayman Beaches and Cayman Crystal Caves are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Grand Cayman Blow Holes and Rum Point Beach.

What’s a holiday rental in Old Man Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Man Bay. Holiday rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.