Old Man Bay Vacation Rentals from CA $126: Short-Term Rentals for 2026

A cave with stalactites and stalagmites, a shallow pool of water, and rock formations.

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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

North Side

Elizabeth

CA $716 total

includes taxes & fees

Dec 1 - Dec 2

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

Annette

CA $265 total

includes taxes & fees

Nov 16 - Nov 17

A beach with two white lounge chairs and a blue umbrella.

3. Galleon Villas by Hello Cayman Vacation

Seven Mile Beach

Matthew

CA $1,063 total

includes taxes & fees

Nov 23 - Nov 24

An indoor garden with seating areas, plants, and hanging lights.

4. Cayman Luxury Rentals at The Grove

Seven Mile Beach

tracey

CA $682 total

includes taxes & fees

Nov 17 - Nov 18

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

North Side

Jami G.

CA $507 total

includes taxes & fees

Nov 13 - Nov 14

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

Patricks Island

Matt D.

CA $230 total

includes taxes & fees

Nov 13 - Nov 14

A two-story house with a swimming pool in the foreground.

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

George Town

luis M.

CA $358 total

includes taxes & fees

Nov 14 - Nov 15

A two-story house with a beige facade, large windows, and a brick driveway.

8. Casa de Bells 3

Patricks Island

CA $375 total

includes taxes & fees

Nov 16 - Nov 17

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

Savannah

Emma

CA $311 total

includes taxes & fees

Nov 16 - Nov 17

A clear turquoise sea with rocky formations and a sandy beach.

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

South Sound

Francesca E.

CA $347 total

includes taxes & fees

Dec 1 - Dec 2

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

Savannah

Renee M.

CA $244 total

includes taxes & fees

Nov 13 - Nov 14

A beach with palm trees, a hammock, and lounge chairs.

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

Rum Point

Michelle G.

CA $644 total

includes taxes & fees

Nov 21 - Nov 22

A beach with white lounge chairs, palm trees, and a clear blue ocean.

13. Cayman Luxury Rentals at Coral Bay

Savannah

CA $1,310 total

includes taxes & fees

Nov 30 - Dec 1

A resort with a central pool, palm trees, and beachfront views.

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

Rum Point

Jacob B.

CA $666 total

includes taxes & fees

Dec 5 - Dec 6

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and modern buildings.

15. Cayman Luxury Rentals at One Canal Point

Seven Mile Beach

Kathleen

CA $868 total

includes taxes & fees

Dec 3 - Dec 4

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

Savannah

Stephanie H.

CA $362 total

includes taxes & fees

Nov 13 - Nov 14

A wooden boardwalk leading to a gazebo by the beach.

17. Oceanfront Peace 2BR with Wave Views

Patricks Island

Janielle

CA $302 total

includes taxes & fees

Nov 17 - Nov 18

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

George Town

Richard L.

CA $878 total

includes taxes & fees

Dec 10 - Dec 11

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

West Bay

Jamie S.

CA $446 total

includes taxes & fees

Nov 24 - Nov 25

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

Grand Harbour

Cynthia

CA $550 total

includes taxes & fees

Nov 16 - Nov 17

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Top Old Man Bay Hotel Reviews

On The Bay

North Side

10/10 Excellent

Rose Ann

An aerial view of a resort with multiple buildings, a swimming pool, and a beach.

The Locale Hotel Grand Cayman

Seven Mile Beach

10/10 Excellent

Staff are lovely and welcoming - and very helpful. Rooms are spacious. Beds are comfortable, including nice pillows. Showers are roomy and bathrooms very clean. Close to many good restaurants and shops. Walkable to Camana Bay and beach (near The Sovereign). Hotel itself is not on the beach, but we drive to our preferred beaches or walk to the beach using the public path near The Sovereign. A short drive to the Fosters at Camana Bay for groceries. Good parking behind the hotel. Pool and...

Anthony

A beach with two lounge chairs and a beach umbrella.

Hampton by Hilton Grand Cayman Seven Mile Beach

Seven Mile Beach

10/10 Excellent

Anthony

A room with a large window, a bed with white bedding, and a view of the beach.

Hotel Indigo Grand Cayman by IHG

Seven Mile Beach

10/10 Excellent

Olena

A beach resort with a pier extending into turquoise waters, a pool, and sun loungers.

Cobalt Coast Resort

Northwest Point

10/10 Excellent

Samantha

An infinity pool with lounge chairs and umbrellas, overlooking a sunset over the ocean with buildings in the background.

ONE GT Grand Cayman

George Town

10/10 Excellent

My family of 4 stayed at OneGT for a week in grand cayman island in a standard room. We really enjoyed the hotel and its available pools and amenities. The hotel is only 5months old so everything is spotlessly clean and the room has high end, clean appliances allocated for our use. There was a fridge/freezer, microwave, washer/dryer, dishwasher and full oven with all amenities of a home kitchen. There’s also a high end coffee maker with complimentary coffee/tea/milk which was throughly enjoyed...

Keith

A resort with a large pool, palm trees, and a view of the ocean.

Kimpton Seafire Resort + Spa by IHG

Seven Mile Beach

10/10 Excellent

Megan

Galleon Villas by Hello Cayman Vacation

Seven Mile Beach

10/10 Excellent

Hello Cayman Vacation Condo rentals at Villas of the Galleon are lovely. The property is kept immaculate with beautiful seasonal flowers and bushes. The staff work very hard to ensure a wonderful time for those who stay here. The seven mile beach in front of the condos was beautiful and provided a great walk anytime of the day. The ocean was nice to experience although at times it was a little tricky getting in and out due to the shelf of sand etc in the water due to some rough winds. We met...

Sharene

A hotel courtyard with a fountain, palm trees, and a pool area.

Grand Cayman Marriott Beach Resort

Seven Mile Beach

10/10 Excellent

Jason

A seaside terrace with lounge chairs, a glass balustrade, and a view of the ocean.

The Ritz-Carlton, Grand Cayman

Seven Mile Beach

10/10 Excellent

Anonymous traveller

A resort pool area with lounge chairs, palm trees, and a view of the ocean.

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Seven Mile Beach

10/10 Excellent

Paolo

A resort with a pool, beach area, and lounge chairs.

The Sunshine Hotel and Suites

Seven Mile Beach

10/10 Excellent

Melody

A clear pool with palm trees and a sunset in the background.

The Grand Caymanian Resort

West Bay

10/10 Excellent

Barbara

A resort pool with a cabana, palm trees, and a view of the ocean.

Morritts Tortuga Club

East End

10/10 Excellent

I came with a lot of anxiety after reading many negative reviews. Was I pleasantly surprised when I entered the suite. The furniture is dated, but is pleasant and in reasonable conditions. The kitchen is well equipped. Hotel meals are expensive. There's a Foster's grocery close to hotel. Cooking own meals saved a lot of $. The strength of this resort is location right on water front. Beach is not great, but you can snorkel right off beach. Plenty of fish right under pier. No coral to speak...

David

A beachside resort with a thatched gazebo, palm trees, and a clear view of the ocean.

Holiday Inn Resort Grand Cayman by IHG

West Bay

10/10 Excellent

Cayman Luxury Rentals at One Canal Point

Seven Mile Beach

8/10 Good

The on line check in was a nightmare was not able to get into the property until 500 p.m. There was no contact directly and we had to wait for calls back. There was a process whereby check in code would not let us check in. The online contact number did not provide anything else. Although to give them credit the people worked on a solution and reset the apartment code. If you are a computer expert then maybe decide to book here. Condo nice and clean. On line check in a nightmare. Going on...

Peter

Cayman Luxury Rentals at The Grove

Seven Mile Beach

10/10 Excellent

Monika

Find out more about Old Man Bay

Everything you need to know about Old Man Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Old Man Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Man Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Man Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Man Bay. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Man Bay vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Old Man Bay vacation rentals we have selected for you start as low as CA $126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Old Man Bay rentals

At Expedia, we put the best Old Man Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Old Man Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Man Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Man Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Old Man Bay Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Old Man Bay vacation rentals

1. On The Bay

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

3. Galleon Villas by Hello Cayman Vacation

4. Cayman Luxury Rentals at The Grove

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

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

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

8. Casa de Bells 3

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

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

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

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

13. Cayman Luxury Rentals at Coral Bay

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

15. Cayman Luxury Rentals at One Canal Point

16. Beautiful one bedroom apartment

17. Oceanfront Peace 2BR with Wave Views

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

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

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

Find vacation rentals that suit your style

Top Old Man Bay Hotel Reviews

On The Bay

10/10 Excellent

Find out more about Old Man Bay

Old Man Bay vacation rentals: An excellent choice for every season

How to find incredible deals on Old Man Bay rentals

Frequently Asked Questions

Are there vacation rentals in Old Man Bay?

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

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

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

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

Explore a world of travel with Expedia