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Our top choices for Old Man Bay holiday rentals

On The Bay

On The Bay
4.0 star property
North Side
10.0 out of 10, Exceptional, (6 reviews)
"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 £799
includes taxes & fees
17 Feb - 18 Feb
On The Bay

Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool
North Side
9.0 out of 10, Wonderful, (2 reviews)
"This was our second time to Cayman and the 2nd time staying at "On the Bay" condos.We had a fabulous stay. It was nicely appointed and well-maintained.This condo is the perfect spot for vacationing...far from the hustle and bustle of Georgetown but close enough to go over for sightseeing, food, and drink.Then return to the "quieter side of the island with enough local food and drink to ease into the night."
United States
S L.
The price is £583
includes taxes & fees
17 Feb - 18 Feb
Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

Spacious 2-Bedroom 2-Bathroom Beachfront Condo with Heated Pool

Spacious 2-Bedroom 2-Bathroom Beachfront Condo with Heated Pool
North Side
9.4 out of 10, Exceptional, (13 reviews)
"Our 3rd visit here, always good, love the property and location."
United States
Anonymous traveller
The price is £580
includes taxes & fees
21 Feb - 22 Feb
Spacious 2-Bedroom 2-Bathroom Beachfront Condo with Heated Pool

Pease Bay House Cayman Islands

Pease Bay House Cayman Islands
Grand Cayman
10.0 out of 10, Exceptional, (1 review)
"The house itself was absolutely beautiful and the location on the beach with both sunrise and sunset views was incredible. We have 4 children and had another family joined us with their 2 children and we had the best time. Lots of clean sandy beach area to play, plus fun coral area to explore. Be sure to bring water shoes to make it easy to explore. Host was super helpful with recommendations and response time was very quick. We truly enjoyed our stay!"
United States
Aileen R.
The price is £4,140
includes taxes & fees
15 Feb - 16 Feb
Pease Bay House Cayman Islands

Country Road, Take me Home- your own Island Cottage!

Country Road, Take me Home- your own Island Cottage!
Savannah
9.4 out of 10, Exceptional, (11 reviews)
"The Shower and 5g internet stood out. It was a very pleasant stay "
United States
Cody
The price is £138
includes taxes & fees
19 Feb - 20 Feb
Country Road, Take me Home- your own Island Cottage!

Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands

Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands
Savannah
10.0 out of 10, Exceptional, (4 reviews)
"Great stay in Savannah"
United States
Onkar P.
The price is £183
includes taxes & fees
10 Feb - 11 Feb
Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands

Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach

Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach
Bt
10.0 out of 10, Exceptional, (4 reviews)
"Had a great stay"
United States
Annette
The price is £167
includes taxes & fees
15 Feb - 16 Feb
Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach

Beautiful 3 Bd Beachfront Home North Side Sleeps 7

Beautiful 3 Bd Beachfront Home North Side Sleeps 7
North Side
10.0 out of 10, Exceptional, (7 reviews)
"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 £771
includes taxes & fees
25 Feb - 26 Feb
Beautiful 3 Bd Beachfront Home North Side Sleeps 7

Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!
Patricks Island
8.4 out of 10, Very good, (22 reviews)
"Excellent stay. Very peaceful and easy instructions "
Canada
raymond
The price is £118
includes taxes & fees
19 Feb - 20 Feb
Slice of Paradise- 2 mins from Spotts Beach!

1BD 1.5BA Convenient and Cosy Apartment with Pool

1BD 1.5BA Convenient and Cosy Apartment with Pool
George Town
10.0 out of 10, Exceptional, (1 review)
"Great location to get all over the island, convenient services nearby, dedicated parking spot, easy entry and the pool temperature was great. "
United States
Sonja B.
1BD 1.5BA Convenient and Cosy Apartment with Pool

Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking

Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
George Town
9.8 out of 10, Exceptional, (64 reviews)
"Great pool. Nice and private "
Canada
Bradley
The price is £191
includes taxes & fees
10 Feb - 11 Feb
Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking

Ocean/Beachfront - stunning views! Seabreeze Villas

Ocean/Beachfront - stunning views! Seabreeze Villas
Bodden Town
9.6 out of 10, Exceptional, (24 reviews)
"Stunning and breathtaking, unobstructed views of the beach. Great pool for the kids with pool amenities such as, floaties. Kids loved it! We all had such a blast. We definitely recommend Seabreeze Villas."
United States
Renee
The price is £520
includes taxes & fees
27 Feb - 28 Feb
Ocean/Beachfront - stunning views! Seabreeze Villas

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

The Pink Beach House - Private House and Pool directly on the Beach, Rum Point
Rum Point
9.8 out of 10, Exceptional, (180 reviews)
"My husband and I stayed here to celebrate our 4th wedding anniversary and we had a fabulous time. The house had everything you could ever need for vacation. The area is absolutely beautiful. This place is a 10/10!!!! "
United States
Morgan A.
The price is £730
includes taxes & fees
21 Feb - 22 Feb
The Pink Beach House - Private House and Pool directly on the Beach, Rum Point

Beautiful one bedroom apartment

Beautiful one bedroom apartment
Savannah
9.4 out of 10, Exceptional, (11 reviews)
"Nice little place, quiet and peaceful. A bit away from restaurants and shopping."
Canada
Nathalie B.
The price is £194
includes taxes & fees
16 Feb - 17 Feb
Beautiful one bedroom apartment

Ocean Paradise

Ocean Paradise
4.0 star property
North Side
9.6 out of 10, Exceptional, (38 reviews)
"Wonderful property! We enjoyed our stay very much! "
United States
Ashley
Ocean Paradise

Luxury 3bd Beach Front, # 4 Green, Stunning Views

Luxury 3bd Beach Front, # 4 Green, Stunning Views
North Side
9.6 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay! The house is steps to a small beach and a stone’s throw from Rum Point. Perfect situation."
United States
Louise R.
The price is £907
includes taxes & fees
15 Feb - 16 Feb
Luxury 3bd Beach Front, # 4 Green, Stunning Views

Luxury 3bd Beach View, # 3 Blue, Stunning Views

Luxury 3bd Beach View, # 3 Blue, Stunning Views
North Side
9.6 out of 10, Exceptional, (21 reviews)
"Very clean, quite and had all we needed."
United States
Rachel W.
Luxury 3bd Beach View, # 3 Blue, Stunning Views

Cayman Luxury Rentals at One Canal Point

Cayman Luxury Rentals at One Canal Point
4.0 star property
Seven Mile Beach
10.0 out of 10, Exceptional, (6 reviews)
"The property is pristine! We had a great stay! "
United States
Kathleen
The price is £956
includes taxes & fees
15 Feb - 16 Feb
Cayman Luxury Rentals at One Canal Point

Cayman Luxury Rentals at Sunset Cove

Cayman Luxury Rentals at Sunset Cove
3.5 star property
Seven Mile Beach
The price is £1,733
includes taxes & fees
8 Feb - 9 Feb
Cayman Luxury Rentals at Sunset Cove

Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio

Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio
Grand Harbour
9.6 out of 10, Exceptional, (4 reviews)
"Very responsive host, beautiful view"
United States
Elizabeth
The price is £301
includes taxes & fees
15 Feb - 16 Feb
Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio
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, apart-hotels, 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 favorite 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 depends 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 £186 per night. Entering your travel dates in the search wizard you might find 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 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 Star Fish Point.

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.