Photo by Paul Shaffer -Dee

Old Man Bay Holiday Rentals

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Old Man Bay holiday rentals

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 S$1,111
includes taxes & fees
18 Jan - 19 Jan, 2026
On The Bay
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
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 S$3,432
includes taxes & fees
16 Jan - 17 Jan, 2026
Cayman Luxury Rentals at Sunset Cove
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers
Governors Village Seven Mile Beach Corridor

Apartment in Seven Mile Beach

Governors Village Seven Mile Beach Corridor
3.5 star property
9.6 out of 10, Exceptional, (271)
"Absolutely, amazing would highly recommend your stay there!"
United States
Renita
The price is S$957
includes taxes & fees
5 Jan - 6 Jan, 2026
Governors Village Seven Mile Beach Corridor
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

Wyndham Reef Resort - All Inclusive

Wyndham Reef Resort - All Inclusive

10/10 Excellent
"The staff was fantastic! Everyone on the whole property was extremely nice and accommodating. "
David 7-night trip
Posted 4 days ago
Wyndham Reef Resort - All Inclusive

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.