Old Man Bay Vacations from $739

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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!

The Latest Old Man Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
Price was $1,046, price is now $739 per person
$739
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (1,000 reviews)
I had the best vacation ever at the Kimpton Seafire! The staff was exceptional, and the level of service was unlike anything I have ever experienced, and I travel often. I traveled solo to celebrate my retirement and the team went above and beyond to make my stay truly unforgettable. From the warm welcome to the thoughtful touches throughout my visit, every detail exceeded my expectations. Thank you for making such a special milestone even more memorable. I will definitely be back soon!

Reviewed on Jul 29, 2026

The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

3.5 out of 5
Save 100% on your flight
Price was $1,957, price is now $1,046 per person
$1,046
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.4/10 Very Good! (1,084 reviews)

Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
Price was $3,271, price is now $2,004 per person
$2,004
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
10/10 Exceptional! (3 reviews)

Point West Premier Rentals

Point West Premier Rentals

4 out of 5
Northwest Point
Price was $1,341, price is now $943 per person
$943
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,743, price is now $1,253 per person
$1,253
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (764 reviews)

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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.
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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

$55
per adult
98% of travellers recommend
Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point
Stingray Sandbar, Snorkeling, and Starfish Point

Stingray Sandbar, Snorkeling, and Starfish Point

$60
per adult
100% of travellers recommend
Stingray Sandbar, Snorkeling, and Starfish Point
Guests swimming in the bio bay

Grand Cayman - Bioluminescent Bay Tour

$115
per adult
94% of travellers recommend
Grand Cayman - Bioluminescent Bay Tour
See all activities in Old Man Bay

Old Man Bay Hotel Deals

On The Bay

On The Bay

4 out of 5
67 Old Robin Rd North Side North Side
Get rates
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

Get rates
Beach House and Cottage with 2 Full Kitchens, Sleeps 16.
See all 1,474 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.

Find the Best Old Man Bay Vacation Packages

Old Man Bay Essential Information

Language
English
Closest Airport
Owen Roberts Intl. Airport (GCM)
Top Sights
Starfish Beach, Rum Point Beach and Star Fish Point

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Frequently asked questions

How much does an Old Man Bay vacation package cost?
You'll find cheap prices from $739 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?
January, September and December are great times to look for cheap Old Man Bay vacation packages. Traveling in quieter periods means you can usually find better prices on hotels and flights.
How many days is enough for Old Man Bay?
The ideal duration for your Old Man Bay vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to hit all the major attractions and explore some hidden gems along the way.
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. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to Old Man Bay.
  2. Budget wisely: On top of the price of your stay, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Old Man Bay.
  3. Discover Old Man Bay using our trip planning tool: Gain insights into the leading attractions and best properties for your trip to Old Man Bay. You can also save your favorite locations, collaborate with friends and family and arrange all your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Old Man Bay, you can work out the right length of your break. Put together a draft itinerary and allocate enough time for all the things you want to do.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick an Old Man Bay vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Old Man Bay's best offerings. Find all the fun things to do in Old Man Bay with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Old Man Bay vacation packages?
Your Old Man Bay break is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.