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Old Man Bay Holiday Rentals

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Our top choices for Old Man Bay holiday rentals

1. Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation
3.5 star property
Seven Mile Beach
10.0 out of 10, Exceptional, (210 reviews)
"We loved the spacious unit and the view of the water. The beach was wonderful. Also, the recommendations provided by the host were spot on and great. We used the kitchen every morning for breakfast and the start of the day. We will definitely go back -- The only "issue" was the complex did not have a swimming pool --"
United States
Matthew
The price is NZ$1,391
includes taxes & fees
9 Oct - 10 Oct
Galleon Villas by Hello Cayman Vacation

2. Cayman Luxury Rentals at The Grove

Cayman Luxury Rentals at The Grove
3.5 star property
Seven Mile Beach
9.2 out of 10, Wonderful, (60 reviews)
"excellent location and great property to stay for getting to know Grand Caymen. Property is across the street from a beautiful beach and within walking distance to restaurants/ coffee shops. "
Canada
tracey
The price is NZ$705
includes taxes & fees
11 Oct - 12 Oct
Cayman Luxury Rentals at The Grove

3. Cayman Luxury Rentals at Coral Bay

Cayman Luxury Rentals at Coral Bay
3.0 star property
Savannah
The price is NZ$1,510
includes taxes & fees
4 Nov - 5 Nov
Cayman Luxury Rentals at Coral Bay

4. Cayman Luxury Rentals at One Canal Point

Cayman Luxury Rentals at One Canal Point
4.0 star property
Seven Mile Beach
9.4 out of 10, Exceptional, (8 reviews)
"The property is pristine! We had a great stay! "
United States
Kathleen
The price is NZ$2,077
includes taxes & fees
23 Oct - 24 Oct
Cayman Luxury Rentals at One Canal Point

5. Villas Pappagallo 17

Villas Pappagallo 17
2.0 star property
West Bay
10.0 out of 10, Exceptional, (1 review)
"I love being able to walk out of my room straight on to the beach, this place is at the most northern point on the island, you can watch the sun rise and sunset, it’s not a commercial headache, far away from the regular tourists"
United States
Andrew
The price is NZ$748
includes taxes & fees
9 Oct - 10 Oct
Villas Pappagallo 17

6. Cayman Luxury Rentals at Lighthouse Point Residences

Cayman Luxury Rentals at Lighthouse Point Residences
3.5 star property
Northwest Point
9.4 out of 10, Exceptional, (3 reviews)
"A very perfect place!"
United States
Kirk Thomas
The price is NZ$1,362
includes taxes & fees
10 Oct - 11 Oct
Cayman Luxury Rentals at Lighthouse Point Residences

7. Grape Tree Villas 30

Grape Tree Villas 30
2.0 star property
Seven Mile Beach
The price is NZ$955
includes taxes & fees
14 Oct - 15 Oct
Grape Tree Villas 30

8. The Grove 33 in Grand Cayman

The Grove 33 in Grand Cayman
2.0 star property
Seven Mile Beach
The price is NZ$933
includes taxes & fees
14 Oct - 15 Oct
The Grove 33 in Grand Cayman

9. George Town Villas 116

George Town Villas 116
2.0 star property
Seven Mile Beach
The price is NZ$1,008
includes taxes & fees
14 Oct - 15 Oct
George Town Villas 116

10. Cocoplum 9 in George Town

Cocoplum 9 in George Town
2.0 star property
Seven Mile Beach
The price is NZ$1,118
includes taxes & fees
9 Oct - 10 Oct
Cocoplum 9 in George Town

11. Villas of the Galleon 4

Villas of the Galleon 4
2.0 star property
Seven Mile Beach
The price is NZ$1,152
includes taxes & fees
13 Oct - 14 Oct
Villas of the Galleon 4

12. Villas of the Galleon 6

Villas of the Galleon 6
2.0 star property
Seven Mile Beach
The price is NZ$1,242
includes taxes & fees
13 Oct - 14 Oct
Villas of the Galleon 6

13. George Town Villas 117

George Town Villas 117
2.0 star property
Seven Mile Beach
George Town Villas 117

14. George Town Villas 118

George Town Villas 118
2.0 star property
Seven Mile Beach
The price is NZ$1,271
includes taxes & fees
10 Oct - 11 Oct
George Town Villas 118

15. Cocoplum 10 in George Town

Cocoplum 10 in George Town
2.0 star property
Seven Mile Beach
The price is NZ$1,346
includes taxes & fees
9 Oct - 10 Oct
Cocoplum 10 in George Town

16. Sunset Point 29 in West Bay

Sunset Point 29 in West Bay
2.0 star property
Northwest Point
The price is NZ$790
includes taxes & fees
21 Oct - 22 Oct
Sunset Point 29 in West Bay

17. S4 BP Steps to Beach Entire Apartment

S4 BP Steps to Beach Entire Apartment
2.0 star property
West Bay
The price is NZ$811
includes taxes & fees
1 Nov - 2 Nov
S4 BP Steps to Beach Entire Apartment
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Old Man Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Old Man Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Old Man Bay. Seeing all the best attractions is bound to make you fall in love with Old Man Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Old Man Bay short-term rentals, that won’t be hard to do.

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?

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!: This holiday home rental outside of Old Man Bay is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Cayman Kai Public 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.