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 $1,764, price is now CA $1,043 per person
CA $1,043
per person
Oct 1 - Oct 5
found 22 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
8.4/10 Very good! (1,084 reviews)

Black Urchin

Black Urchin

4.5 out of 5
Price was CA $8,931, price is now CA $5,340 per person
CA $5,340
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
10/10 Exceptional! (3 reviews)

Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Price was CA $1,731, price is now CA $1,149 per person
CA $1,149
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.8/10 Exceptional! (764 reviews)

The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Price was CA $1,887, price is now CA $1,314 per person
CA $1,314
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.2/10 Wonderful! (1,003 reviews)
Excellent in every aspect, clean, nicely staff, property condition, for me, is 10/10

Reviewed on Jul 28, 2026

Point West Premier Rentals

Point West Premier Rentals

4 out of 5
Northwest Point
Price was CA $1,580, price is now CA $1,115 per person
CA $1,115
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to George Town (GCM)
9.8/10 Exceptional! (21 reviews)
This condo was absolutely 💯 beautiful. We got upgraded to the penthouse suite and it was incredible with breathtaking views .... we would definitely stay here again.

Reviewed on Jul 29, 2026

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
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On The Bay
The Place

The Place

4 out of 5
110 Old Robin Rd Old Man Bay North Side
10/10 Exceptional! (13 reviews)
"Beautiful place with a clean, comfortable stay and everything we needed and even more. The check-in and check-out instructions were very clear and easy to follow. Parking was available, and the private entrance made everything feel convenient and secure. The location is excellent, close to spots ..."

Reviewed on May 27, 2026

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The Place
Beach House and Cottage with 2 Full Kitchens, Sleeps 16.

Beach House and Cottage with 2 Full Kitchens, Sleeps 16.

Old Man Bay North Side
10/10 Exceptional! (13 reviews)
"Very nice and clean,host very responsive and communication always prompt. Loved our stay!"

Reviewed on Jul 20, 2026

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Beach House and Cottage with 2 Full Kitchens, Sleeps 16.
See all 1,475 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.
All Inclusive Vacations
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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
Guests swimming in the bio bay

Grand Cayman - Bioluminescent Bay Tour

CA $163
per adult
94% of travellers recommend
Grand Cayman - Bioluminescent Bay Tour
Small Group E-Bike Grand Cayman Ecological Half-Day Tour

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

CA $183
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 $1,043 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.