Old Man Bay Vacations from $913
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Hotel Indigo Grand Cayman by IHG
$913
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (797 reviews)
We absolutely loved our stay at Hotel Indigo Grand Cayman. Everything was exceptional—from the beautiful, modern hotel and comfortable rooms to the wonderful service and relaxing atmosphere.
Pom Pom was superb! The rooftop setting, views, drinks, and atmosphere were fantastic and definitely one of the highlights of our stay.
Rasa was amazing as well. The food was delicious, beautifully presented, and the service was excellent. We enjoyed every meal there.
The breakfast buffet at Catalinas as well.
The entire staff was friendly, welcoming, and attentive throughout our stay. The hotel has a great location near Seven Mile Beach, a beautiful pool area, and such a stylish yet relaxed Caribbean vibe.
We truly enjoyed everything about our experience and would definitely return. Highly recommend Hotel Indigo Grand Cayman!
Reviewed on Aug 10, 2026
The Reef Beach Resort, East End, Grand Cayman
$1,036
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.4/10 Very Good! (1,084 reviews)
Unfortunately our stay was the same week that was plagued by insurmountable seaweed on the beach, causing terrible smells. We know this isn’t the resorts fault, but they did eventually have trucks out to remove it after a few days. We did not do an all inclusive option, so the breakfast buffet was rather expensive per person. Drinks at the beach bar were great. Not aware that maid service wasn’t automatic and that placing the maid service tag on your door did not mean they would actually stop by and perform main service so recommend calling the front desk to schedule cleaning as needed. Overall, we had a great stay. Just wish a little bit more communication during check-in about maid service was available. Very convenient that there was a fosters across the street.
Reviewed on Aug 10, 2026
Cayman Luxury Rentals at Ocean Paradise
$1,318
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (43 reviews)
Family friendly, very equipped accommodation. Caring and quick responsive staff. Would definitely recommend the place.
Reviewed on Jul 11, 2026
Don't see what you're looking for?
See all available trips from Columbus to Old Man Bay
View all tripsStay 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.
What to do in Old Man Bay
Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point
$55
per adult
98% of travellers recommend
Stingray Sandbar, Snorkeling, and Starfish Point
$60
per adult
100% of travellers recommend
Horseback Beach Riding in the Grand Cayman
$100
per adult
94% of travellers recommend
Old Man Bay Hotel Deals
The Place
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
Beach House and Cottage with 2 Full Kitchens, Sleeps 16.
Old Man Bay North Side
10/10 Exceptional! (14 reviews)
"We had a wonderful stay! The host was so nice, quick to respond and very helpful with suggestions! Both houses were well equipped and beds super comfortable. We enjoyed the swings, hammocks and pool by the ocean!"
Reviewed on Aug 4, 2026
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 |
More vacations you might like
Frequently asked questions
How much does an Old Man Bay vacation package cost?
You'll find cheap prices from $913 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
