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.
Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

4.5 out of 5
Price was $958, price is now $739 per person
$739
per person
Jul 1 - Jul 4
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (571 reviews)
It would have been nice if there was live music available by the pool and some planned activities. Also, a shuttle to go to different areas around the island would have been easier than taking cabs.

Reviewed on Apr 11, 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 20 hours 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

Club Suites at Rum Point

Club Suites at Rum Point

4 out of 5
Price was $3,007, price is now $2,205 per person
$2,205
per person
May 21 - May 25
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

Reef Resort Grand Cayman

Reef Resort Grand Cayman

3.5 out of 5
Price was $1,042, price is now $776 per person
$776
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

Morritt's Grand

Morritt's Grand

2.5 out of 5
Save 100% on your flight
Price was $1,649, price is now $1,269 per person
$1,269
per person
May 31 - Jun 5
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.8/10 Excellent! (3 reviews)
Property was very clean and service was friendly.

Reviewed on Mar 10, 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! (9 reviews)
The place was perfect with the exception of being one bedroom. Based on the photos we thought it was two bedrooms, but there is a couch sofa. Its also not walking distance to the tourist areas or shops. It was normally a 30 minute commute to our activities. The place was very modern and clean. The ...

Reviewed on Mar 24, 2026

Get rates
The Place
On The Bay

On The Bay

4 out of 5
67 Old Robin Rd North Side North Side
$582 nightly
The price is $631 total per night from Apr 13 to Apr 14
$631 total
Apr 13 - Apr 14
Total with taxes and fees
10/10 Exceptional! (8 reviews)
Looking forward to going back!

Reviewed on Apr 6, 2026

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! (6 reviews)
We had everything we needed in one cottage or the other. Host was very attentive to our needs and any questions about activities. Had one minor issue with hot water that was attended to immediately. Loved the quiet location with easy access to everything the Grand Caymans had to offer.

Reviewed on Mar 25, 2026

Get rates
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 $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.