Old Man Bay Holidays

Photo by Paul Shaffer -Dee
    deals illustration
    Better together
    Save up to S$134 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Old Man Bay

On The Bay
On The Bay
4 out of 5
67 Old Robin Rd, North Side, North Side
The price is S$1,027 per night from 26 Jun to 27 Jun
S$1,027
26 Jun - 27 Jun
includes taxes & fees
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 23 May, 2025

On The Bay
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 S$1,474 per night from 6 Jul to 7 Jul
S$1,474
6 Jul - 7 Jul
includes taxes & fees
9.4/10 Exceptional! (992 reviews)
"10000/10 It’s the Ritz ! What a great experience"

Reviewed on 14 Jun, 2025

The Ritz-Carlton, Grand Cayman
Hampton by Hilton Grand Cayman Seven Mile Beach
Hampton by Hilton Grand Cayman Seven Mile Beach
4 out of 5
22 Piper Way, Seven Mile Beach
The price is S$366 per night from 11 Jul to 12 Jul
S$366
11 Jul - 12 Jul
includes taxes & fees
9/10 Wonderful! (552 reviews)
"It looks great after remodeling"

Reviewed on 18 Jun, 2025

Hampton by Hilton Grand Cayman Seven Mile Beach
See all 1,426 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 holiday 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 holiday 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 holiday 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 holiday. 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," "Traveller 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Old Man Bay holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can personalise 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 holiday 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 holiday package that brings all your bookings together.

What to do in Old Man Bay

Grand Cayman Bioluminescence Adventure

Grand Cayman Bioluminescence Adventure

S$204
per adult
Grand Cayman Bioluminescence Adventure
Grand Cayman Bioluminescent Bay Adventure

Grand Cayman Bioluminescent Bay Adventure

S$192
per adult
Grand Cayman Bioluminescent Bay Adventure
Private Guided Boat Charters in The Cayman Islands

Private, Guided Boat Charters in The Cayman Islands

S$643
per traveller
Private, Guided Boat Charters in The Cayman Islands
See all activities in Old Man Bay

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.