Old Man Bay Vacation Packages

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Your Old Man Bay Vacation

Come and experience this wonderful city for yourself with a Old Man Bay vacation package. Think about staying in the neighborhood of Breakers, which is great for culture and coastal beaches, and your time here is sure to be unforgettable. You'll want to do a little exploring during your trip to Old Man Bay. Carve out some time for big-name attractions such as Queen Elizabeth II Botanic Park, Cayman Kai Public Beach and Mastic Trail South Trailhead. Stop dreaming and start doing. Browse the multitude of options on Expedia today and put your Old Man Bay vacation plans into motion!

Top Old Man Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

3.5 out of 5
Price was CA $2,706, price is now CA $1,643 per person
CA $1,643
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to George Town (GCM)
8.4/10 Very good! (1,101 reviews)
Loved the walkout except at night when sound travelled into the unit from the pool, adjoining decks like they were in the building. Linens could be improved….old, poor quality. Great people/staff. Stay here often because of them.

Reviewed on Oct 26, 2026

The Grove and The Grove Too

The Grove and The Grove Too

5 out of 5
Price was CA $4,512, price is now CA $2,417 per person
CA $2,417
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.6/10 Exceptional! (268 reviews)

Point West Premier Rentals

Point West Premier Rentals

4 out of 5
Northwest Point
Price was CA $5,647, price is now CA $3,437 per person
CA $3,437
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.8/10 Exceptional! (29 reviews)
The room is in excellent conditions, Host is very nice and easy to communicate with. The rooms are very spacious as well as the living room and kitchen. Private Parking under roof.

Reviewed on Oct 26, 2026

ONE GT Grand Cayman

ONE GT Grand Cayman

4.5 out of 5
Price was CA $4,652, price is now CA $2,944 per person
CA $2,944
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
10/10 Exceptional! (45 reviews)

Black Urchin

Black Urchin

4.5 out of 5
Price was CA $18,987, price is now CA $12,758 per person
CA $12,758
per person
Dec 6 - Dec 13
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to George Town (GCM)
10/10 Exceptional! (3 reviews)

Ready to book your vacation to Old Man Bay?

 

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Old Man Bay Hotel Deals

On The Bay

On The Bay

4 out of 5
67 Old Robin Rd North Side North Side
The price is CA $346 per night from Dec 1 to Dec 2
CA $346
CA $706 total
Dec 1 - Dec 2
includes taxes & fees
On The Bay
The Place

The Place

4 out of 5
110 Old Robin Rd Old Man Bay North Side
10/10 Exceptional! (15 reviews)
"Great place to stay, no issues whatsoever. Great host, brand new place, kitchen has everything even spices and cooking oil!!! I would recommend to stay there during a visit."

Reviewed on Sep 19, 2026

Get rates
The Place
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

5 out of 5
West Bay Road Seven Mile Beach Grand Cayman
Fully refundableReserve now, pay when you stay
The price is CA $1,118 per night from Nov 29 to Nov 30
CA $1,118
CA $1,529 total
Nov 29 - Nov 30
includes taxes & fees
The Ritz-Carlton, Grand Cayman
See all 1,480 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.
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Stay near popular Old Man Bay attractions

Cayman Crystal Caves

Commune with nature and explore the great outdoors at Cayman Crystal Caves during your travels in Old Man Bay.
See properties

What to do in Old Man Bay

Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point

Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point

CA $78
per adult
98% of travellers recommend
Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point
Beautiful Stingrays on sandbar.

Starfish Point, Stingray City & Coral Garden (3-STOP Adventure)

CA $113
per adult
100% of travellers recommend
Starfish Point, Stingray City & Coral Garden (3-STOP Adventure)
Small Group E-Bike Grand Cayman Ecological Half-Day Tour

Small Group E-Bike Grand Cayman Ecological Half-Day Tour

CA $182
per adult
Small Group E-Bike Grand Cayman Ecological Half-Day Tour
See all activities in Old Man Bay

Frequently asked questions

How much does an Old Man Bay vacation package cost?
You can snap up a vacation package to this destination from CA $1,643 on Expedia. However, how much your vacation to Old Man Bay costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Old Man Bay?
Plan your getaway for the off-season and you're likely to find cheap Old Man Bay vacation packages. Remember that public holidays and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Old Man Bay?
With around 7 days, you'll have plenty of time to enjoy popular neighbourhoods such as Breakers and Brinkleys during your Old Man Bay vacation. Remember to also add Mastic Trail North Trailhead and Mastic Trail South Trailhead to your sightseeing itinerary. Searching for more adventures? Consider exploring outside of Old Man Bay on tours and day trips.
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 budget, add a few filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Old Man Bay package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Old Man Bay vacation as a package?
You can enjoy significant savings on your Old Man Bay retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Old Man Bay?
If you're considering an impromptu Old Man Bay vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Old Man Bay?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Old Man Bay.
  2. Plan your budget wisely: In addition to the price of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Old Man Bay.
  3. Decide how long to go away for: Now that you know more about Old Man Bay, you can work out the ideal length of your vacation. Pull together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Old Man Bay vacation package.

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