Old Man Bay Vacations from $781

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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.
Reef Resort Grand Cayman

Reef Resort Grand Cayman

3.5 out of 5
Price was $1,047, price is now $781 per person
$781
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.4/10 Very Good! (1,047 reviews)
Loved our stay here.

Reviewed on Apr 7, 2026

Point West Premier Rentals

Point West Premier Rentals

4 out of 5
Northwest Point
Save 100% on your flight
Price was $1,227, price is now $802 per person
$802
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (11 reviews)
Beautiful place with covered parking. Elevator, ice box, and equipped kitchen made this a great stay. Great host! Ten minute drive to Seven Mile Beach, highly recommend.

Reviewed on Apr 5, 2026

The Sunshine Hotel and Suites

The Sunshine Hotel and Suites

4 out of 5
Save 100% on your flight
Price was $1,198, price is now $855 per person
$855
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
Third time staying here and it gets better every time! They recently renovated and the new rooms are really nice! With two little kids, it was nice to have a little kitchen to store and reheat as needed. We arrived 2 hours early and they accommodated us quickly which was very helpful with little kids! The short walk the Westing and having all the restaurants right by us were a huge plus! We can’t wait to go back!

Reviewed on Apr 12, 2026

Aqua Bay Club Condos

Aqua Bay Club Condos

3 out of 5
Save 100% on your flight
Price was $2,237, price is now $1,629 per person
$1,629
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (90 reviews)
We stayed on the end condo on the ground floor. It was very clean and well stocked with comfy furnishings and amazing views! Claudette was so kind and helpful in the office along with the other girl. We sat in the screened in porch and watched the ocean and was able to snorkel right outside our condo. We will certainly stay again! The only minor negative was that the West end is pretty far away from restaurants and shopping so we took the public bus for those things.

Reviewed on Mar 1, 2026

Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Save 100% on your flight
Price was $2,304, price is now $1,687 per person
$1,687
per person
May 20 - May 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.4/10 Exceptional! (28 reviews)
Great place to stay. The frontage is rocky so it is not easy to walk right into the ocean but there is a ladder off the pier to enter for snorkeling. Rum Point is just around the corner- can walk on the beach or road to get to it and is a lot calmer and out of the wind. I would say the only negative was being farther away from a lot of the tourist things and snorkeling we wanted to do.

Reviewed on Apr 3, 2026

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Discover the most popular places to visit in Old Man Bay

Starfish Beach

Starfish Beach

4.5/5(296 reviews)

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

Queen Elizabeth II Botanic Park

4/5(10 reviews)

Enjoy the beautiful coral reefs and explore Queen Elizabeth II Botanic Park, a lovely green space in Breakers. Stroll along the beautiful beaches in this relaxing area, or check out its lively bars.

Queen Elizabeth II Botanic Park

Mastic Trail North Trailhead

3/5(3 reviews)

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

Mastic Trail North 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

$65
per adult
100% of travellers recommend
Stingray City Sandbar, Coral Gardens Snorkeling & Star Fish Point
Starfish Point, Stingray City-Sandbar & Coral Gardens

Starfish Point, Stingray City-Sandbar & Coral Gardens

$65
per adult
96% of travellers recommend
Starfish Point, Stingray City-Sandbar & Coral Gardens
Horseback Beach Riding in the Grand Cayman

Horseback Beach Riding in the Grand Cayman

$100
per adult
92% of travellers recommend
Horseback Beach Riding in the Grand Cayman
See all activities in Old Man Bay

Old Man Bay Hotel Deals

The Place

The Place

4 out of 5
110 Old Robin Rd Old Man Bay North Side
10/10 Exceptional! (10 reviews)
It was easy to check in and get the key . The Place is a well prepared for travelers . Even if you forgott something they have it . It is like your own home . Everything is in order . Nice setup . Clean . Owner is a sweetheart. Restaurant , giftshop , gas station , liquor store is in walking distance ...

Reviewed on Apr 13, 2026

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The Place
On The Bay

On The Bay

4 out of 5
67 Old Robin Rd North Side North Side
10/10 Exceptional! (8 reviews)
Looking forward to going back!

Reviewed on Apr 6, 2026

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On The Bay
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! (7 reviews)
What an amazing propery, host and home! We had a fantastic stay with plenty to do for everyone from ages 7 to 80. The house was clean and what a beautiful location. Morne was filled with great recommendations for food and activities. The only thing to keep in mind is that the beach isn't swimmable ...

Reviewed on Apr 12, 2026

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Beach House and Cottage with 2 Full Kitchens, Sleeps 16.
See all 1,466 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 $781 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.