Old Man Bay Vacations from $989

Book a Hotel + Flight or Car together to unlock savings

Photo by Paul Shaffer -Dee

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.
ONE Canal Point

ONE Canal Point

3.5 out of 5
Save 100% on your flight
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (144 reviews)
Great stay! Excellent!

Reviewed on Jul 27, 2025

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
Save 100% on your flight
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (846 reviews)
Property was beautiful & the staff was amazing

Reviewed on Aug 3, 2025

Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
Save 100% on your flight
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.4/10 Very Good! (1,008 reviews)
Dated property, not as pictured when selecting a location to stay on line. Request made several times for fresh towels but was not done, went to front desk for assistance.

Reviewed on Jul 30, 2025

Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation

3.5 out of 5
Save 100% on your flight
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
10/10 Exceptional! (194 reviews)
This place is fantastic! The beach is just a few steps away, our villa was clean and modern and within walking distance of restaurants. Everyone was friendly and helpful. They went above and beyond to make our vacation a relaxing one. We will definitely be returning.

Reviewed on Jul 8, 2025

Black Urchin

Black Urchin

4.5 out of 5
Save 100% on your flight
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
10/10 Exceptional! (2 reviews)
Property is Beautiful and very private. One downside is being so far from extracurricular activities

Reviewed on Mar 26, 2025

Don't see what you're looking for?
See all available trips from Columbus to Old Man Bay
View all trips

Discover the most popular places to visit in Old Man Bay

If you’ve ever wanted to touch starfish, go to Starfish Point in Grand Cayman. Always keep the starfish in water. Pick them up and flip them over but set them down gently right side up. #LifeAtExpedia #GrandCayman #Starfish #OceanLife

Starfish Beach

If a restful vacation is part of your travel plans, Starfish Beach might be the perfect place to seek out during your trip to Rum Point. Wander the area's seaside or simply enjoy one of its seafood restaurants.

Starfish Beach
Wander the botanic park and gardens or tour the Blue Iguana Recovery Program. More on www.ajauntwithjoy.com

Queen Elizabeth II Botanic Park

Enjoy the beautiful coral reefs and explore Queen Elizabeth II Botanic Park, a lovely green space in Breakers. Stroll along the seaside in this relaxing area, or check out its top-notch restaurants.

Queen Elizabeth II Botanic Park

Mastic Trail South Trailhead

Explore the lovely green spaces of Mastic Trail South Trailhead and enjoy the snorkeling spots in Breakers. Wander the beautiful beaches and seaside in this relaxing area.

Mastic Trail South Trailhead

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
100% of travellers recommend
Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point
Heading over to Bio Bay

Grand Cayman - Bioluminescent Bay Tour

$95
per adult
84% of travellers recommend
Grand Cayman - Bioluminescent Bay Tour
Stingray Sandbar, Snorkeling, and Starfish Point

Stingray Sandbar, Snorkeling, and Starfish Point

$56
per adult
100% of travellers recommend
Stingray Sandbar, Snorkeling, and Starfish Point
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
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 May 23, 2025

Get rates
On The Bay
The Bay with 500 Feet of BeachFront and 2 Cottages

The Bay with 500 Feet of BeachFront and 2 Cottages

Old Man Bay
"The Property is wonderful and exceeded our expectations! There were 13 of us on vacation and every one of us had a more than comfortable place to sleep. The two facilities were spotless and were laid out beautifully. The Hosts were courteous and accommodating. We received great advice from them during ..."

Reviewed on Jul 27, 2025

Get rates
The Bay with 500 Feet of BeachFront and 2 Cottages
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
32 Seafire Way, Seven Mile Beach, West Bay
Fully refundable
$369 nightly
The price is $413 total per night from Aug 20 to Aug 21
$413 total
Aug 20 - Aug 21
Total includes taxes and fees
9.6/10 Exceptional! (333 reviews)
"5 stars all around."

Reviewed on Aug 5, 2025

Hotel Indigo Grand Cayman by IHG
See all 1,437 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Old Man Bay vacation package cost?
You'll find cheap prices from $989 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.