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Old Man Bay Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Old Man Bay vacation rentals

A beach with palm trees, a hammock, and a clear blue sky.

1. On The Bay

On The Bay
4.0 star property
North Side
10.0 out of 10, Exceptional, (12 reviews)
"Looking forward to going back! "
United States
Elizabeth
The price is ￥39,164
￥79,773 total
includes taxes & fees
Dec 1 - Dec 2
On The Bay
A coastal view with a beach, palm trees, and a gazebo.

2. Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach

Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach
Bt
9.4 out of 10, Exceptional, (10 reviews)
"Had a great stay"
United States
Annette
The price is ￥14,079
￥29,392 total
includes taxes & fees
Nov 17 - Nov 18
Relax and Unwind at our cozy 1-bedroom Apt, within mins away from the beach
A beach with two white lounge chairs and a blue umbrella.

3. Galleon Villas by Hello Cayman Vacation

Galleon Villas by Hello Cayman Vacation
3.5 star property
Seven Mile Beach
10.0 out of 10, Exceptional, (210 reviews)
"We loved the spacious unit and the view of the water. The beach was wonderful. Also, the recommendations provided by the host were spot on and great. We used the kitchen every morning for breakfast and the start of the day. We will definitely go back -- The only "issue" was the complex did not have a swimming pool --"
United States
Matthew
The price is ￥100,336
￥118,397 total
includes taxes & fees
Nov 23 - Nov 24
Galleon Villas by Hello Cayman Vacation
An indoor garden with seating areas, plants, and hanging lights.

4. Cayman Luxury Rentals at The Grove

Cayman Luxury Rentals at The Grove
3.5 star property
Seven Mile Beach
9.2 out of 10, Wonderful, (60 reviews)
"excellent location and great property to stay for getting to know Grand Caymen. Property is across the street from a beautiful beach and within walking distance to restaurants/ coffee shops. "
Canada
tracey
The price is ￥45,449
￥83,267 total
includes taxes & fees
Nov 17 - Nov 18
Cayman Luxury Rentals at The Grove
A beach scene with a thatched umbrella and a lounge chair on the sand.

5. The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point

The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point
North Side
9.6 out of 10, Exceptional, (15 reviews)
"The host was absolutely wonderful - very quick to respond and super helpful. Highly recommend for a quiet, laid-back vacation!!! "
United States
Jami G.
The price is ￥32,392
￥56,196 total
includes taxes & fees
Nov 13 - Nov 14
The Big Chill - Beach Cottage at The Sea Lodges in Cayman Kai / Rum Point
Interior

6. Slice of Paradise- 2 mins from Spotts Beach!

Slice of Paradise- 2 mins from Spotts Beach!
Patricks Island
8.4 out of 10, Very good, (31 reviews)
"Quiet and convenient, was exactly what we needed for a nights stay!!!!"
United States
Matt D.
The price is ￥22,121
￥25,755 total
includes taxes & fees
Nov 13 - Nov 14
Slice of Paradise- 2 mins from Spotts Beach!
A two-story house with a swimming pool in the foreground.

7. Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking

Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
George Town
9.8 out of 10, Exceptional, (71 reviews)
"The host was really nice and the stay was perfect"
United States
luis M.
The price is ￥23,702
￥41,794 total
includes taxes & fees
Nov 12 - Nov 13
Casa de Bells 2 - Studio apartment with pool, gazebo, private entrance & parking
A two-story house with a beige facade, large windows, and a brick driveway.

8. Casa de Bells 3

Casa de Bells 3
Patricks Island
The price is ￥23,702
￥41,794 total
includes taxes & fees
Nov 11 - Nov 12
Casa de Bells 3
A modern two-story house with a well-lit entrance, a small front yard, and a driveway.

9. Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands

Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands
Savannah
9.8 out of 10, Exceptional, (11 reviews)
"Excellent stay! "
United States
Emma
The price is ￥19,909
￥34,446 total
includes taxes & fees
Nov 23 - Nov 24
Charming 1-bedroom apartment in enchanting Savannah, Cayman Islands
A clear turquoise sea with rocky formations and a sandy beach.

10. Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove

Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
South Sound
9.8 out of 10, Exceptional, (116 reviews)
"Amazing place!"
United States
Francesca E.
The price is ￥25,124
￥38,977 total
includes taxes & fees
Dec 1 - Dec 2
Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
Beach

11. Country Road, Take me Home- your own Island Cottage!

Country Road, Take me Home- your own Island Cottage!
Savannah
9.2 out of 10, Wonderful, (16 reviews)
"Great location’"
Canada
Renee M.
The price is ￥17,381
￥27,336 total
includes taxes & fees
Nov 13 - Nov 14
Country Road, Take me Home- your own Island Cottage!
A beach with palm trees, a hammock, and lounge chairs.

12. "Mai Kai" Recently renovated Oceanfront Ground Floor Condo - Kaibo Yacht Club II

"Mai Kai" Recently renovated Oceanfront Ground Floor Condo - Kaibo Yacht Club II
Rum Point
10.0 out of 10, Exceptional, (62 reviews)
"We had a fabulous stay and enjoyed the time we spent there."
United States
Michelle G.
The price is ￥37,922
￥71,294 total
includes taxes & fees
Nov 22 - Nov 23
"Mai Kai" Recently renovated Oceanfront Ground Floor Condo - Kaibo Yacht Club II
A beach with white lounge chairs, palm trees, and a clear blue ocean.

13. Cayman Luxury Rentals at Coral Bay

Cayman Luxury Rentals at Coral Bay
3.0 star property
Savannah
The price is ￥89,858
￥145,122 total
includes taxes & fees
Nov 30 - Dec 1
Cayman Luxury Rentals at Coral Bay
A resort with a central pool, palm trees, and beachfront views.

14. Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot Tub

Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot Tub
Rum Point
9.4 out of 10, Exceptional, (6 reviews)
"This was the perfect spot for a quiet weekend getaway."
United States
Jacob B.
The price is ￥29,864
￥72,917 total
includes taxes & fees
Dec 5 - Dec 6
Newly Renovated 2 Bed Beachfront Condo w/Pool+Hot Tub
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and modern buildings.

15. Cayman Luxury Rentals at One Canal Point

Cayman Luxury Rentals at One Canal Point
4.0 star property
Seven Mile Beach
9.4 out of 10, Exceptional, (8 reviews)
"The property is pristine! We had a great stay! "
United States
Kathleen
The price is ￥52,902
￥96,671 total
includes taxes & fees
Dec 3 - Dec 4
Cayman Luxury Rentals at One Canal Point
A building with a pink facade, a well-maintained garden with artificial grass and potted plants, and a palm tree.

16. Beautiful one bedroom apartment

Beautiful one bedroom apartment
Savannah
9.6 out of 10, Exceptional, (17 reviews)
"The location is in a quiet neighborhood in the middle of the island, so easy to get to anywhere. Also close to Spotts Beach for snorkeling. The hosts were very friendly and helpful. "
United States
Stephanie H.
The price is ￥22,516
￥39,981 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful one bedroom apartment
A wooden boardwalk leading to a gazebo by the beach.

17. Oceanfront Peace 2BR with Wave Views

Oceanfront Peace 2BR with Wave Views
Patricks Island
10.0 out of 10, Exceptional, (1 review)
"This property is outstanding Great view of the ocean exelent amenities comfortable beds,comfortable sofa.Will definately recomend to everyone"
United States
Janielle
The price is ￥30,815
￥33,509 total
includes taxes & fees
Nov 16 - Nov 17
Oceanfront Peace 2BR with Wave Views
A resort with a central swimming pool, multiple guest rooms, and a view of the ocean.

18. BE WHERE THE CRUISE SHIP CROWDS CAN'T GO! Oceanfront resort on Seven Mile Beach

BE WHERE THE CRUISE SHIP CROWDS CAN'T GO! Oceanfront resort on Seven Mile Beach
George Town
9.8 out of 10, Exceptional, (111 reviews)
"Good location with private beach access. "
United States
Richard L.
The price is ￥63,046
￥95,576 total
includes taxes & fees
Dec 10 - Dec 11
BE WHERE THE CRUISE SHIP CROWDS CAN'T GO! Oceanfront resort on Seven Mile Beach
A resort with multiple buildings, each with a red-tiled roof, surrounded by well-maintained gardens and palm trees, overlooking a calm sea.

19. Quiet Ground-Floor Beachfront 1BR w/ Pool

Quiet Ground-Floor Beachfront 1BR w/ Pool
West Bay
10.0 out of 10, Exceptional, (1 review)
"Perfect and a great price."
Canada
Jamie S.
The price is ￥14,537
￥45,975 total
includes taxes & fees
Nov 11 - Nov 12
Quiet Ground-Floor Beachfront 1BR w/ Pool
A row of colorful houses reflecting on calm water, with a cloudy sky above.

20. Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio

Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio
Grand Harbour
9.8 out of 10, Exceptional, (6 reviews)
"The photos on the site do not do this condo justice. It is much nicer then the photos make it look. Really clean, had plenty of towels, quite spacious, nice little deck looking at the water, convenient to shops and restaurants and lovely pool. Would definitely stay here again! "
United States
Cynthia
The price is ￥41,952
￥60,837 total
includes taxes & fees
Nov 17 - Nov 18
Waterfront Sanctuary Serene, Grand Harbour, 2 Bed, 2 Bath, Pool, Patio
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.
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Top Old Man Bay Hotel Reviews

Hotel Indigo Grand Cayman by IHG

Hotel Indigo Grand Cayman by IHG

10/10 Excellent
"Perfect location, best beach on 7 mile to crystal clear waters a short walk across the street.They offer bike rental that makes this stay even better and so easy to get around island. Swimming pools clean and refreshing, pool service great!"
Dan 7-night trip
Posted 3 hours ago
Hotel Indigo Grand Cayman by IHG

Find out more about Old Man Bay

Search for holiday rentals in Old Man Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Man Bay using one of the methods below:

  • View our selection of featured holiday rentals in Old Man Bay
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  • Enter your travel dates to view the best deals on holiday rentals in Old Man Bay while they last

Look no further and take a look at our great range of rental properties in Old Man Bay!

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?

Reef Romance, Rum Point Oceanfront Villa with Private Pool and Gorgeous Beach!: This vacation home rental outside of Old Man Bay is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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

Choose from 9 Expedia vacation rentals in Old Man Bay for a memorable vacation.

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

Grand Cayman Beaches and Cayman Crystal Caves are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Grand Cayman Blow Holes and Cayman Kai Public 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.