Old Man Bay Vacations from $872

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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.
Wyndham Reef Resort Grand Cayman

Wyndham Reef Resort Grand Cayman

3.5 out of 5
Price was $1,294, price is now $872 per person
$872
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.4/10 Very Good! (1,014 reviews)
The room and the entire facility was clean and well kept. Staff was friendly and attentive. Pools and beach were clean and well kept. Ocean view is terrific!

Reviewed on Feb 24, 2026

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

5 out of 5
Save 100% on your flight
Price was $4,186, price is now $2,707 per person
$2,707
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (953 reviews)
The room was great! I loved the view and the pillows were great. The night lights in the room are unique. I loved the frozen grapes and popsicles they hand out on the beach. I fell pampered. Great and such kind people. Loved my stay!

Reviewed on Feb 4, 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 $2,841, price is now $1,849 per person
$1,849
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9.8/10 Exceptional! (432 reviews)
Staff were so friendly and helpful, very clean rooms, restaurants were excellent and the resort is beautiful!

Reviewed on Feb 21, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $2,424, price is now $1,609 per person
$1,609
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
It was sooooo busy! Could hardly get a beach chair. Didn’t honor my Marriott Ambassador status because I booked on Expedia (missed out on points and breakfast). Room and bed was comfy. Won’t be returning.

Reviewed on Feb 17, 2026

Morritts Tortuga Club

Morritts Tortuga Club

3.5 out of 5
Price was $1,573, price is now $1,067 per person
$1,067
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to George Town (GCM)
8.2/10 Very Good! (336 reviews)
We loved our stay at Morritts which i on the east side of an island with qiet and very local.atmosphere. The resort is by the beautiful beach and has a 3 pools and also hot tubs. It is very clean and staff is nice and helpful. Restaurants are on site. They also offer activities. It has all we needed to relax and enjoy our stay.

Reviewed on Jan 22, 2026

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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 top-notch restaurants.

Starfish Beach

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

$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
Stingray Sandbar, Snorkeling, and Starfish Point

Stingray Sandbar, Snorkeling, and Starfish Point

$63
per adult
100% of travellers recommend
Stingray Sandbar, Snorkeling, and Starfish Point
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! (3 reviews)
Loved the stay here.

Reviewed on Feb 17, 2026

Get rates
The Place
On The Bay

On The Bay

4 out of 5
67 Old Robin Rd North Side North Side
$782 nightly
The price is $853 total per night from Mar 14 to Mar 15
$853 total
Mar 14 - Mar 15
Total with taxes and fees
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

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! (4 reviews)
House was very clean and with beautiful outdoor spaces. The cottage is newer and the original house is bigger, plenty of room for our group of 13 age range 7 to 74. It was nice to have different activities amd relaxing spaces for everyone (bags, soccer, pool, beach, different lounge areas). The hosts ...

Reviewed on Jan 25, 2026

Get rates
Beach House and Cottage with 2 Full Kitchens, Sleeps 16.
See all 1,470 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 $872 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.