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Old Man Bay Holiday Rentals

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Our top choices for Old Man Bay holiday rentals

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 AU$1,257
includes taxes & fees
18 Jan - 19 Jan 2026
On The Bay
8.0 out of 10, Very good, (1)
"Pool was fantastic. Location was lovely and quiet. Andre was very helpful on Christmas Eve with an emergency service issue. "
United States
Beth G.
The price is AU$985
includes taxes & fees
18 Jan - 19 Jan 2026
Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

Apartment in Seven Mile Beach

Governors Village Seven Mile Beach Corridor
3.5 star property
9.6 out of 10, Exceptional, (275)
"Absolutely, amazing would highly recommend your stay there!"
United States
Renita
The price is AU$1,112
includes taxes & fees
5 Jan - 6 Jan 2026
Governors Village Seven Mile Beach Corridor
10.0 out of 10, Exceptional, (2)
"We were lucky to have such a nice host. Tiffany is very hospitable. My mother has a disability and Tiffany adjusted to her needs, e.g. she brought us chairs so my mom could sit down to put her clothes on and feel more independent. (Big positive) The apartment was very clean on arrival and the AC works people !! Although it is close to the beach it is not as close as the ad suggests , it would be 5 minutes by car . By foot the beach is 20 minutes away. Which wasn’t a problem for me but my mom was...
United States
L J.
The price is AU$325
includes taxes & fees
12 Jan - 13 Jan 2026
Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach

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
2.0 star property
9.4 out of 10, Exceptional, (11)
"The Shower and 5g internet stood out. It was a very pleasant stay "
United States
Cody
The price is AU$275
includes taxes & fees
8 Jan - 9 Jan 2026
Country Road, Take me Home- your own Island Cottage!
10.0 out of 10, Exceptional, (6)
"Beautiful villa- just as described. If you prefer quiet away from SMB this villa is perfect. It was just my husband and I for the week and it was lovely - plenty of of space for the whole family if we had the kids with us. Thanks for a great stay!"
United States
Jessica D.
The price is AU$1,409
includes taxes & fees
29 Jan - 30 Jan 2026
Chic Family Friendly 3 Bed 2 Bath Beach Front Home
10.0 out of 10, Exceptional, (2)
"Great stay in Savannah"
United States
Onkar P.
The price is AU$355
includes taxes & fees
12 Jan - 13 Jan 2026
Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands

Holiday Home in Patricks Island

Slice of Paradise- 2 mins from Spotts Beach!
8.2 out of 10, Very good, (20)
"Excellent stay. Very peaceful and easy instructions "
Canada
raymond
The price is AU$257
includes taxes & fees
5 Jan - 6 Jan 2026
Slice of Paradise- 2 mins from Spotts Beach!
9.8 out of 10, Exceptional, (62)
"Great pool. Nice and private "
Canada
Bradley
The price is AU$379
includes taxes & fees
6 Jan - 7 Jan 2026
Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
10.0 out of 10, Exceptional, (2)
"This was the perfect spot for a quiet weekend getaway."
United States
Jacob B.
The price is AU$2,134
includes taxes & fees
3 Jan - 4 Jan 2026
Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot Tub

Apartment in Savannah

Beautiful one bedroom apartment
9.6 out of 10, Exceptional, (8)
"Nice little place, quiet and peaceful. A bit away from restaurants and shopping."
Canada
Nathalie B.
The price is AU$418
includes taxes & fees
15 Jan - 16 Jan 2026
Beautiful one bedroom apartment
3.5 star property
10.0 out of 10, Exceptional, (203)
"Our go to place at the Cayman Islands. Best location with the best beach and water just few steps from the terrace. Large kitchen and living room. Service room is excellent cleaning everything every day, including fresh beach towels. "
United States
Ludmila
The price is AU$1,806
includes taxes & fees
5 Jan - 6 Jan 2026
Galleon Villas by Hello Cayman Vacation

Apartment in Seven Mile Beach

Cayman Luxury Rentals at The Grove
3.5 star property
9.2 out of 10, Wonderful, (54)
"Modern room. Great location"
Canada
Tamas
Cayman Luxury Rentals at The Grove
9.8 out of 10, Exceptional, (13)
"Beautiful location, house was roomy and comfortable with everything you need to relax."
United States
Julie W.
The price is AU$1,814
includes taxes & fees
14 Jan - 15 Jan 2026
Luxury 3bd Ocean View, # 1 Cream, Stunning Views
9.8 out of 10, Exceptional, (32)
"Easy check-in, and the kitchen is updated. "
United States
Matthew J.
The price is AU$1,155
includes taxes & fees
4 Jan - 5 Jan 2026
Luxurious 2 Bdr Beachfront Villa - Coral Beach House - Excellent Cayman value!
9.6 out of 10, Exceptional, (21)
"Very clean, quite and had all we needed."
United States
Rachel W.
The price is AU$1,939
includes taxes & fees
16 Jan - 17 Jan 2026
Luxury 3bd Beach View, # 3 Blue, Stunning Views
10.0 out of 10, Exceptional, (60)
"Well kept and beautiful views."
United States
Hilary R.
The price is AU$2,138
includes taxes & fees
15 Jan - 16 Jan 2026
Luxury 3bd Beach Front, # 5 Yellow, Stunning Views
9.4 out of 10, Exceptional, (3)
"Very responsive host, beautiful view"
United States
Elizabeth
The price is AU$724
includes taxes & fees
15 Jan - 16 Jan 2026
Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio

Holiday Home in Prospect Park

Tranquil Breeze no cleaing fee
6.0 out of 10, (2)
"We really enjoyed our stay. The unit was brand new and clean. I think they are just in the process of rehab the entire property. The bed was a bit too soft for my taste, but the linens were brand new and clean. If it had a few coffee mugs and utensils that would be perfect The shampoo/conditioner & body was a very nice touch. I would stay again!"
United States
Jennifer K.
The price is AU$328
includes taxes & fees
2 Jan - 3 Jan 2026
Tranquil Breeze no cleaing fee
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

Find out more about Old Man Bay

Everything you need to know about Old Man Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Old Man Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Man Bay holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Old Man Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Man Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Man Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Old Man Bay holiday rentals we have selected for you start as low as AU$1,112 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Old Man Bay rentals

At Expedia, we put the best Old Man Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Old Man Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Man Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Man Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.