Old Man Bay Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Paul Shaffer -Dee
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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Old Man Bay Vacation Packages

Old Man Bay Hotel Deals

On The Bay

On The Bay

4 out of 5
67 Old Robin Rd, North Side, North Side
10/10 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!"

Reviewed on May 23, 2025

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On The Bay
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
32 Seafire Way, Seven Mile Beach, West Bay
Fully refundable
The price is ₩330,804 per night from Jul 21 to Jul 22
₩330,804
₩503,398 total
Jul 21 - Jul 22
includes taxes & fees
9.6/10 Exceptional! (294 reviews)
"Beautiful property! Fabulous staff! Perfect location"

Reviewed on Jul 14, 2025

Hotel Indigo Grand Cayman by IHG
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road, PO Box 32348 KY1-1209, Seven Mile Beach, Grand Cayman
The price is ₩911,371 per night from Aug 6 to Aug 7
₩911,371
₩1,259,282 total
Aug 6 - Aug 7
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Amazing place , we are going to comeback soon!"

Reviewed on Jul 12, 2025

The Ritz-Carlton, Grand Cayman
See all 1,431 properties in Old Man Bay
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.

Frequently asked questions

How much does an Old Man Bay vacation package cost?
You'll find cheap prices on Expedia for your Old Man Bay escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Old Man Bay costs.
What are the cheapest months to go to Old Man Bay?
The off-season is the best time to head to Old Man Bay if you're hoping to keep costs down. Another tip for finding cheap Old Man Bay vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Old Man Bay?
Usually, a handful of days is enough to see the main sights during your Old Man Bay vacation. However, if you want to have more time to chill out or go on day trips, think about extending your itinerary.
How to find the best Old Man Bay package deals?
Landing a cheap Old Man Bay package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Old Man Bay package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Old Man Bay vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can personalize your Old Man Bay escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Old Man Bay?
If you're considering a spur-of-the-moment Old Man Bay adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Old Man Bay?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred season and the type of activities available will also help you decide when to escape to Old Man Bay.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will probably be the biggest expense during your trip to Old Man Bay.
  3. Determine how many days away: Start by listing all the sights and activities you'd like to experience in Old Man Bay. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find an Old Man Bay vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.