Photo by Paul Shaffer -Dee

Old Man Bay Vacation Rentals

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Vacation Rentals in Old Man Bay

On the beach, white sand, sun loungers, beach umbrellas
Villas of the Galleon
2.5 star property
9.8 out of 10, Exceptional, (71)
"Excellent place to stay!"
Villas of the Galleon
Private beach, white sand, free beach cabanas, sun loungers
Galleon Villas by Hello Cayman Vacation
3.5 star property
10.0 out of 10, Exceptional, (132)
"Short walk from room to water. "
The price is CA $675
CA $796 total
includes taxes & fees
Jun 2 - Jun 3
Galleon Villas by Hello Cayman Vacation
3 Bedroom Villa - Ocean Front # 624 | Terrace/patio
Regal Beach Club
4.0 star property
9.6 out of 10, Exceptional, (216)
"Beautiful condo, great location, walking distance to Camana Bay and other shops and dining. We will be back!"
Regal Beach Club
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Exercise/lap pool
ONE Canal Point
3.5 star property
10.0 out of 10, Exceptional, (71)
"Staff were really helpful. Walkable to the beach"
ONE Canal Point
Outdoor pool, free cabanas, pool umbrellas
Caribbean Club Luxury Condo Hotel
5.0 star property
9.8 out of 10, Exceptional, (45)
"Excellent Property. Their front desk team needs some working on because they give couldn't care less attitude."
Caribbean Club Luxury Condo Hotel
Pool
Ocean Front Paradise Seven Mile Beach Sunsets!
9.8 out of 10, Exceptional, (142)
"Wonderful trip!"
Ocean Front Paradise Seven Mile Beach Sunsets!
Property grounds
Sunset Cove
3.5 star property
9.0 out of 10, Wonderful, (161)
"Sunset Cove Condominiums is a gorgeous property, and is located perfectly on 7 Mile Beach. We paid for an island view room, but were given an ocean view room without even asking. Not sure why, but I never look a gift horse in the mouth. Anyway, the room was beautiful, the property was extremely clean, and we will definitely be back in the future!"
Sunset Cove
Beach
Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
9.8 out of 10, Exceptional, (59)
"I was looking for a location within walking distance of snorkeling spots, and Blair's apt fit the bill to a tee. We needed a place to sleep and shower and this cute, clean and convenient apartment was perfect. We were able to walk to 6 spots from The Lobster Pot down to Smith's Barcadere. The bed was super comfy after a long active day. The kitchen is well appointed and the tub is super deep for soaking sore muscles! Thank you"
Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
On the beach, sun loungers, beach towels
'Cayman Cottage by the Sea' - Family friendly & Budget Price
9.6 out of 10, Exceptional, (57)
"The beach is the high point of this property - lots of lounges, great snorkeling, kayaks, etc."
'Cayman Cottage by the Sea' - Family friendly & Budget Price
A heated pool, sun loungers
Private 7 Mile Beach Beach Club. Ocean views from Roof Terrace and Pool Pavilion
10.0 out of 10, Exceptional, (84)
"Boggy Sands was fantastic! It was in the perfect location in West End, with a private beach fully stocked with chairs, umbrellas, and toys for adults and kids. I would recommend it. Alphonso and "G" were great property and beach managers who were always there if anything was needed and the source of great local restaurant recommendations. Fosters grocery store is a two-minute walk."
Private 7 Mile Beach Beach Club. Ocean views from Roof Terrace and Pool Pavilion
Property grounds
Stunning ,Coastal Chic, apartment in the Heart of 7 mile Beach.
10.0 out of 10, Exceptional, (97)
"I would stay here 100x over. Shevaun and family are the nicest kindest people ever. The place was so wonderful and I wish I lived there. Super easy to get to the beach and to restaurants and grocery store. The property had all the things and more. And I love that it’s called mango trees. I love mangoes and I love trees."
Stunning ,Coastal Chic, apartment in the Heart of 7 mile Beach.
Beach
2 Bedroom Condo Seven Mile Beach -Sunset Cove - Newly Renovated
10.0 out of 10, Exceptional, (55)
"Great property right on the beach. Convenient location walking distance to several restaurants and markets or can hop onto the public bus easily if your looking to go further along 7 mile beach."
The price is CA $525
CA $808 total
includes taxes & fees
Jun 1 - Jun 2
2 Bedroom Condo Seven Mile Beach -Sunset Cove - Newly Renovated
Property grounds
The peace and tranquility of this cottage Works Wonders on the soul....
10.0 out of 10, Exceptional, (48)
"We thoroughly enjoyed our stay. The property is well located and affords privacy will still be close to various attractions. The pool and beach were wonderful, and we enjoyed kayaking and paddle boarding. Would definitely stay again!"
The peace and tranquility of this cottage Works Wonders on the soul....
On the beach, sun loungers, beach towels
Stunning Ocean View Condo steps to 7 Mile Beach-Ground Floor!
10.0 out of 10, Exceptional, (21)
"We enjoyed staying here, loved the location and convenience of the property. The pools on the property were very nice. The beach was unfortunately pretty small, but that's happening in a lot of locations on the south side of 7 Mile right now."
Stunning Ocean View Condo steps to 7 Mile Beach-Ground Floor!
Beach
7th night free, Mi Casa, Su Casa, Beachfront
10.0 out of 10, Exceptional, (123)
"Communication with the host was great. Super attention to detail in the condo. Love the serenity of the location, definitely has a tropical feel. Sunsets were beautiful. Pizza at Solis restaurant next door is great. Would choose again on a repeat visit."
7th night free, Mi Casa, Su Casa, Beachfront
Pool
Steps to the Beach! Water View, 2bed/2.5bath condo - Seabreeze Villas
9.6 out of 10, Exceptional, (23)
"Our nine days in paradise were absolutely spectacular! The condo was perfect and we loved the location as the entire island was within 20 minutes of driving. Our host was very responsive when we arrived and throughout our stay. We hope to come back soon! Our favorite beach on the entire island was this one! Sometimes we had the entire beach to our self. We enjoyed snorkeling. Everyday was a new adventure and saw different marine life including many conch, lobster, puffer fish, a small sting ray,...
Steps to the Beach! Water View, 2bed/2.5bath condo - Seabreeze Villas
View from property
Aqua Bay Club Condos
3.0 star property
9.8 out of 10, Exceptional, (75)
"We absolutely loved it here! The condo was great the staff was friendly and an amazing view!! Snorkeling was awesome just off the beach!"
Aqua Bay Club Condos
A heated pool
Coco Kai Beach Front Villa with Heated Pool and Private Dock
10.0 out of 10, Exceptional, (76)
"Nothing can beat the beautiful ocean views right outside your back door. We enjoyed this property with our 5 kids and 3 grandchildren (ages 1-3). Everyone had the option of going from the beach to the pool, to the kitchen for snacks, to the bed for naps all right there. The house is well equipped with most everything you need. We snorkeled around the north side and decided the snorkeling right out back was some of the best! This gave those antsy people something to do and what beautiful marine...
Coco Kai Beach Front Villa with Heated Pool and Private Dock
Outdoor pool
CALYPSO BLUE: Modern Beachfront Villa with Pool and Beautiful Sunsets!
10.0 out of 10, Exceptional, (93)
"We came to Grand Cayman for my wife’s birthday and had an outstanding time.. Craig is absolutely terrific and very responsive. We had one of our suitcases break and needed a screwdriver. I emailed Craig and in less than 2 minutes, Roy was at the front door with the screwdriver.. The location and condition of the house was very nice, the pool with it beautiful view of the water is exactly what were hoping for!! Not one issue at all.."
CALYPSO BLUE: Modern Beachfront Villa with Pool and Beautiful Sunsets!
Outdoor pool
Private Luxury Waterfront Villa with Pool
10.0 out of 10, Exceptional, (17)
"This house has a great layout and two wings with bedrooms in each. The outdoor pool area is beautiful and peaceful, overlooking the bay. It is fully equipped with a wine fridge, glasses and all the amenities we needed. The only downside was the 9 min walk to seven mile beach (as advertised on vrbo) is across a busy highway with no crosswalks and we could not get to beach without incurring taxi costs."
Private Luxury Waterfront Villa with Pool
Don't see what you're looking for?
See all available 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.

Old Man Bay Vacation Rental Travel Info

Number of vacation rentals
55
Popular accommodation
Old Man Bay private vacation homes
Known landmarks
Rum Point Beach, Starfish Beach and Star Fish Point
International airport
George Town (GCM-Owen Roberts Intl.)

Other types of properties in Old Man Bay you may be interested in

Outdoor wedding area
The Ritz-Carlton, Grand Cayman
5.0 star property
9.6 out of 10, Exceptional, (862)
"Excellent property"
The price is CA $940
CA $1,290 total
includes taxes & fees
Jun 15 - Jun 16
The Ritz-Carlton, Grand Cayman
Outdoor pool
Grand Cayman Marriott Resort
4.5 star property
8.8 out of 10, Excellent, (1001)
"Wow property is super clean. Most friendly and helpful receptionist and staff ever, lovely and great first impression of hotel. Everything about the hotel was exceptional. It was clean, stylish, roomy with excellent service in where we had dinner. Food was good and great value for money and service was attentive and efficient"
The price is CA $474
CA $675 total
includes taxes & fees
Jun 26 - Jun 27
Grand Cayman Marriott Resort
Outdoor pool, free cabanas, pool umbrellas
The Westin Grand Cayman Seven Mile Beach Resort & Spa
4.5 star property
8.6 out of 10, Excellent, (1005)
"Amenities were good. Restaurants were very good. "
The price is CA $722
CA $998 total
includes taxes & fees
Jun 25 - Jun 26
The Westin Grand Cayman Seven Mile Beach Resort & Spa
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Man Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Old Man Bay?

Yes, we offer vacation rentals near top sights in Old Man Bay, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Old Man Bay has to offer?

Blue Vista Villa - Oceanfront 4 Bedroom Pool Home on Northside: This Old Man Bay vacation home rental is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Old Man Bay?

Choose from 10 Expedia vacation rentals in Old Man Bay for a memorable vacation.

What’s there to see and do in Old Man Bay?

Explore the area and family-friendly sights such as Cayman Crazy Golfing Mini Golf, or get out into nature at a spot like Grand Cayman Beaches. In the larger area, you’ll find Grand Cayman Blow Holes and Rum Point Beach.

What’s a vacation rental in Old Man Bay like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Man Bay. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family getaway.

Recent reviews of Old Man Bay properties
Expedia verified reviews