Old Man Bay Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Old Man Bay vacation rentals

Luxury Condo, 3 Bedrooms, Beachfront | Balcony

Cayman Luxury Rentals at Sunset Cove

Cayman Luxury Rentals at Sunset Cove
3.5 star property
Seven Mile Beach
10.0 out of 10, Exceptional, (1 review)
"Couldn’t have enjoyed our stay more. This place is a hidden secret."
United States
Matthew
$1,480 nightly
The price is $1,622
Jun 11 - Jun 12
Total with taxes and fees
Cayman Luxury Rentals at Sunset Cove
Property grounds

Cayman Luxury Rentals at Ocean Paradise

Cayman Luxury Rentals at Ocean Paradise
4.0 star property
North Side
9.6 out of 10, Exceptional, (39 reviews)
"This is very njce place to stay. Very calm and clean property. It is just 45 minutes away from main town but great place to stay. "
United States
Mayur
$621 nightly
The price is $664
Jun 15 - Jun 16
Total with taxes and fees
Cayman Luxury Rentals at Ocean Paradise
Luxury Condo, 2 Bedrooms, Kitchen, Beachfront | Balcony

Cayman Luxury Rentals at Coral Bay

Cayman Luxury Rentals at Coral Bay
2.5 star property
Savannah
$714 nightly
The price is $807
Jun 3 - Jun 4
Total with taxes and fees
Cayman Luxury Rentals at Coral Bay
Private beach, white sand, free beach cabanas, sun loungers

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, (207 reviews)
"Incredible sunsets and lovely sandy beach right outside a modern, spotless condo. "
United States
Westley
$600 nightly
The price is $674
May 23 - May 24
Total with taxes and fees
Galleon Villas by Hello Cayman Vacation
Apartment, Smoking | 1 bedroom

Villas of the Galleon 6

Villas of the Galleon 6
2.0 star property
Seven Mile Beach
$729 nightly
The price is $824
Jun 15 - Jun 16
Total with taxes and fees
Villas of the Galleon 6
Outdoor pool

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
$510 nightly
The price is $554
May 25 - May 26
Total with taxes and fees
Cayman Luxury Rentals at The Grove
Outdoor pool, sun loungers

Cayman Luxury Rentals at Lighthouse Point Residences

Cayman Luxury Rentals at Lighthouse Point Residences
3.5 star property
Northwest Point
9.0 out of 10, Wonderful, (2 reviews)
"Loved everything but Ian (hurricane) "
United States
Danette
$567 nightly
The price is $618
May 27 - May 28
Total with taxes and fees
Cayman Luxury Rentals at Lighthouse Point Residences
Apartment, Smoking | 1 bedroom

Villas of the Galleon 4

Villas of the Galleon 4
2.0 star property
Seven Mile Beach
$596 nightly
The price is $673
May 23 - May 24
Total with taxes and fees
Villas of the Galleon 4
Apartment, Smoking | 2 bedrooms

George Town Villas 118

George Town Villas 118
2.0 star property
Seven Mile Beach
George Town Villas 118
Apartment, Smoking | 2 bedrooms

Cocoplum 10 in George Town

Cocoplum 10 in George Town
2.0 star property
Seven Mile Beach
$671 nightly
The price is $758
May 24 - May 25
Total with taxes and fees
Cocoplum 10 in George Town
Apartment, Smoking | 2 bedrooms

Cocoplum 9 in George Town

Cocoplum 9 in George Town
2.0 star property
Seven Mile Beach
$687 nightly
The price is $776
May 25 - May 26
Total with taxes and fees
Cocoplum 9 in George Town
Apartment, Smoking | 1 bedroom

The Grove 33 in Grand Cayman

The Grove 33 in Grand Cayman
2.0 star property
Seven Mile Beach
$459 nightly
The price is $520
May 24 - May 25
Total with taxes and fees
The Grove 33 in Grand Cayman
Apartment, Smoking | 2 bedrooms

George Town Villas 117

George Town Villas 117
2.0 star property
Seven Mile Beach
$600 nightly
The price is $680
May 29 - May 30
Total with taxes and fees
George Town Villas 117
Apartment, Smoking | 1 bedroom

Sunset Point 29 in West Bay

Sunset Point 29 in West Bay
2.0 star property
Northwest Point
$378 nightly
The price is $428
May 25 - May 26
Total with taxes and fees
Sunset Point 29 in West Bay
Apartment, Accessible, Smoking | 3 bedrooms, desk

S2 BP Steps to Beach Entire Apartment

S2 BP Steps to Beach Entire Apartment
3.0 star property
West Bay
$513 nightly
The price is $580
May 31 - Jun 1
Total with taxes and fees
S2 BP Steps to Beach Entire Apartment
Apartment, Smoking | 1 bedroom

S4 BP Steps to Beach Entire Apartment

S4 BP Steps to Beach Entire Apartment
2.0 star property
West Bay
$437 nightly
The price is $494
Jun 8 - Jun 9
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Man Bay Hotel Reviews

The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

8/10 Good
"Was very pleased with the Ocean Reef which apparently went through change of ownership on April 1st. Note it is no longer a Wyndham Resort Staff were welcoming and all amenities were perfect. East End is another part of Grand Cayman worth exploring."
Colleen 3-night trip
Posted 11 hours ago
The Reef Beach Resort, East End, Grand Cayman

Find out more about Old Man Bay

Everything you need to know about Old Man Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Old Man Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Man Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Old Man Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $664 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Old Man Bay?

Yes, we offer vacation rentals near top sights in Old Man Bay, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Old Man Bay has to offer?

Cayman Luxury Rentals at Ocean Paradise: This vacation home rental outside of Old Man Bay is located by the ocean and has an outdoor pool, a private balcony, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a private yard, and a selection of games so you can immerse yourself in your vacation.

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

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

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 larger area, you’ll find Grand Cayman Blow Holes and Star Fish Point.

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

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Man Bay. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family getaway.